Synthesis and Reactions of Cyclopropenones

Total Page:16

File Type:pdf, Size:1020Kb

Synthesis and Reactions of Cyclopropenones University of Huddersfield Repository Qamar, Muhammad Ilyas Synthesis and Reactions of Cyclopropenones Original Citation Qamar, Muhammad Ilyas (2011) Synthesis and Reactions of Cyclopropenones. Doctoral thesis, University of Huddersfield. This version is available at http://eprints.hud.ac.uk/id/eprint/12304/ The University Repository is a digital collection of the research output of the University, available on Open Access. Copyright and Moral Rights for the items on this site are retained by the individual author and/or other copyright owners. Users may access full items free of charge; copies of full text items generally can be reproduced, displayed or performed and given to third parties in any format or medium for personal research or study, educational or not-for-profit purposes without prior permission or charge, provided: • The authors, title and full bibliographic details is credited in any copy; • A hyperlink and/or URL is included for the original metadata page; and • The content is not changed in any way. For more information, including our policy and submission procedure, please contact the Repository Team at: [email protected]. http://eprints.hud.ac.uk/ Synthesis & Reactions of Cyclopropenones Muhammad Ilyas Qamar A Thesis Submitted to the University of Huddersfield in Partial Fulfilment of the Requirements for the Degree of Doctor of Philosophy University of Huddersfield Department of Chemical & Biological Sciences September 2011 I would like to dedicate this thesis to my mother and father, for their constant love, support and encouragement, they have made many sacrifices, faced many hardships and worked countless hours so that I could have a better life. Without them none of this would be possible. I Contents Contents 1 INTRODUCTION ......................................................................................................... 1 1.1 CYCLOPROPENONES ..................................................................................................... 1 1.2 REACTIONS OF CYCLOPROPENONES .......................................................................... 12 1.2.1 Reaction at the ketone double bond ...................................................................... 12 1.2.2 Reactions across carbon-carbon double bond ...................................................... 13 1.2.3 Reactions with imines: formation of pyrroles ...................................................... 15 1.2.4 Synthesis of six-membered rings .......................................................................... 21 1.2.5 Miscellaneous ....................................................................................................... 24 1.3 PROLOGUE TO THESIS DISCUSSION ............................................................................ 26 2 DISCUSSION ............................................................................................................. 31 2.1 SYNTHESIS OF PYRROLIZIDINES ................................................................................ 32 2.1.1 Synthesis of 5-ethylthio-2,3-diphenyl-1-azabicyclo[3.3.0]oct-2-en-4-one .......... 32 2.1.2 Attempted synthesis of 5-ethoxy-2,3-diphenyl-1-azabicyclo[3.3.0]- oct-2-en-4-one ...................................................................................................... 36 2.1.3 Synthesis of 5-methylthio-2,3-diphenyl-1-azabicyclo[3.3.0]oct-2- en-4-one ................................................................................................................ 37 2.1.4 Synthesis of 5-methoxy-2,3-diphenyl-1-azabicyclo[3.3.0]oct-2-en-4-one .......... 39 2.1.5 Synthesis of 5-methyl-2,3-diphenyl-1-azabicyclo[3.3.0]oct-2-en-4-one ............. 44 2.1.6 Synthesis of 5-methylthio-2,3-diphenyl-8-methyl-1-azabicyclo-[3.3.0]- oct-2-en-4-one ...................................................................................................... 45 2.1.7 Synthesis of 5-methylthio-2,3-diphenyl-8-ethylcarboxylate-1-aza- bicyclo[3.3.0]oct-2-en-4-one ................................................................................ 49 2.1.8 Synthesis of 5-methylthio-2,3-diphenyl-8-(4-methylbenzenesulfonate)- 1-azabicyclo[3.3.0]oct-2-en-4-one ....................................................................... 52 2.1.9 Attempted synthesis of 5-methylthio-2,3-diphenyl-8-hydroxymethyl-1- azabicyclo[3.3.0]oct-2-en-4-one ........................................................................... 54 2.2 REACTIVITY OF PYRROLIZIDINES .............................................................................. 55 2.2.1 Reactivity of 5-methylthio-2,3-diphenyl-1-azabicyclo[3.3.0]-oct-2- en-4-one ................................................................................................................ 55 2.2.2 Reactivity of 5-methoxy-2,3-diphenyl-1-azabicyclo[3.3.0]oct-2-en-4-one ......... 62 2.2.3 Synthesis of 5-hydroxy-2,3-diphenyl-1-azabicyclo[3.3.0]oct-2-en-4-one ........... 64 2.2.4 Attempted synthesis of 5-trifyl-2,3-diphenyl-1-azabicyclo[3.3.0]- oct-2-en-4-one ...................................................................................................... 68 II Contents 2.2.5 Attempted formation of 5-sulfoxy and 5-hydroxy-8-methyl-2,3- diphenyl-1-azabicyclo[3.3.0]oct-2-en-4-one ........................................................ 69 2.2.6 Hydrolysis of 5-methylthio-2,3-diphenyl-8-(4-methylbenzenesulfonate)- 1-azabicyclo[3.3.0]oct-2-en-4-one ....................................................................... 70 2.2.7 Attempted synthesis of 4-butyl-5-ethylthio-2,3-diphenyl-1-azabicyclo- [3.3.0]oct-2-en-4-ol .............................................................................................. 71 2.2.8 Attempted synthesis of 5-ethylthio-2,3-diphenyl-1-azabicyclo-[3.3.0]- oct-2-en-4-ol ......................................................................................................... 71 2.3 SYNTHESIS OF POLYHYDROXYLATED PYRROLIZIDINES ............................................ 72 2.3.1 Synthesis of 2,3-O-isopropylidene-L-erythrose ................................................... 72 2.3.2 Synthesis of (3S,4R)-3,4-isopropylidenedioxypyrroline 1-oxide ......................... 73 2.3.3 Attempted synthesis of 2,3-diphenyl-6,7-isoproylidenedioxy-1-aza- bicyclo[3.3.0]oct-2-en-4-one ................................................................................ 74 2.4 SYNTHESIS OF A HIGHLY SUBSTITUTED , FUNCTIONALISED PYRROLIZIDINE ............ 75 2.4.1 Synthesis of 2-methyl-4-phenyl-5-cyano-1H-pyrroline ....................................... 75 2.4.2 Synthesis of 5-methyl-2,3,7-triphenyl-8-cyano-1-azabicyclo[3.3.0]- oct-2-en-4-one ...................................................................................................... 76 2.5 CYCLOPROPENONES ................................................................................................... 78 2.5.1 Unsubstituted cyclopropenones ............................................................................ 78 2.5.2 Synthesis of dialkylcyclopropenones ................................................................... 83 2.6 ACYCLIC IMINES ......................................................................................................... 88 2.6.1 Synthesis of N-(benzylidene)-tert -butanesulfinamide .......................................... 88 2.6.2 Synthesis of 3-tert -butyl-2-phenyl-1-indenone .................................................... 89 2.6.3 Synthesis of N-(alkylidene)-tert -butanesulfinamides ........................................... 91 2.6.4 Reaction with diphenylcyclopropenone ............................................................... 92 2.7 SYNTHESIS OF INDOLIZIDINES AND PYRROLOAZEPINES ........................................... 93 2.7.1 Indolizidines ......................................................................................................... 93 2.7.2 Pyrroloazepines .................................................................................................... 97 2.8 1,3-DIPOLAR CYCLOADDITIONS ............................................................................... 101 2.8.1 Attempted synthesis of ethyl-5-methylthio-4,1,3-oxadiazobicyclo- [3.3.0]oct-2-ene-2-carboxylate ........................................................................... 101 2.8.2 Synthesis of 4-methoxy-(α-[N-(2-pyrrolidinone)])benzaldoxime ...................... 103 2.8.3 Synthesis of 2-azido-(α-[N-(2-pyrrolidinone)])benzaldoxime ........................... 104 III Contents 2.8.4 Synthesis of 2-[triphenylphosphoranylimino]-α-[N-(2-pyrrolidinone)]- benzaldoxime ...................................................................................................... 105 2.8.5 Synthesis of pyrrolo[1,2-b][1,3]benzodiazin-4-oxime ....................................... 105 2.8.6 Attempted reaction of 2-methylthio-1-pyrroline with a nitrilimine ................... 107 2.9 CONCLUSION & FUTURE WORK .............................................................................. 108 3 EXPERIMENTAL .................................................................................................... 112 3.1 SYNTHESIS OF PYRROLIZIDINES .............................................................................. 112 3.1.1 Synthesis of 5-ethylthio-2,3-diphenyl-1-azabicyclo[3.3.0]oct-2- en-4-one .............................................................................................................. 112 3.1.2 Attempted synthesis of 5-ethoxy-2,3-diphenyl-1-azabicyclo[3.3.0]oct- 2-en-4-one ..........................................................................................................
Recommended publications
  • Experimental and Density Functional Theory Studies of Some Novel Piperidine-Containing Acetylene Glycols
    General Papers ARKIVOC 2016 (iv) 86-99 Experimental and density functional theory studies of some novel piperidine-containing acetylene glycols Amina Mirsakiyeva,a, c, e* Darya Botkina,d, f Karim Elgammal,a, c Assel Ten,f Håkan W. Hugosson,a Anna Delin,a, b, c and Valentina Yue, f a Department of Materials and Nano Physics, School of Information and Communication Technology, KTH Royal Institute of Technology, Electrum 229, SE-16440 Kista, Sweden b Department of Physics and Astronomy, Materials Theory Division, Uppsala University, Box 516, SE-75120 Uppsala, Sweden c Swedish e-Science Research Center (SeRC), KTH Royal Institute of Technology, SE-10044 Stockholm, Sweden d Department of Production Engineering, School of Industrial Engineering and Management, KTH Royal Institute of Technology, Brinellvägen 68, 10044 Stockholm, Sweden e Kazakh-British Technical University, Department of Chemical Engineering, Tole bi 59, 050000 Almaty, Kazakhstan f Institute of Chemical Sciences, Walikhanov str. 106, 050010, Almaty city, Kazakhstan E-mail: [email protected] DOI: http://dx.doi.org/10.3998/ark.5550190.p009.452 Abstract Synthesis routes of novel piperidine-containing acetylenes are presented. The new molecules are expected to exhibit plant growth stimulation properties. In particular, the yield in a situation of drought is expected to increase. Our synthesis makes use of the Favorskii reaction between cyclohexanone/piperidone and triple-bond containing alcohols. The structures of the obtained molecules were determined using nuclear magnetic resonance (NMR). The electronic structure and geometries of the molecules were studied theoretically using first-principles calculations based on density functional theory. The calculated geometries agree very well with the experimentally determined ones, and also allow us to determine bond lengths, angles and charge distributions inside the molecules.
    [Show full text]
  • SYNTHESIS of MODIFIED RIBOSE SPIN-LABEL by KE-WEI CHANG
    SYNTHESIS OF MODIFIED RIBOSE SPIN-LABEL by KE-WEI CHANG Presented to the Faculty of the Graduate School of The University of Texas at Arlington in Partial Fulfillment of the Requirements for the Degree of MASTER OF SCIENCE IN CHEMISTRY THE UNIVERSITY OF TEXAS AT ARLINGTON December 2015 Copyright © by Ke-wei Chang 2015 All Rights Reserved ii Acknowledgements I would like to thank Dr. Frank Foss for giving me the opportunity to work in the field of organic chemistry. He is an excellent teacher and has powerful knowledge of chemistry. He led me to finish our project and gave me tons of advice to improve our experiments. With his guidance, I have learned more than I can learn from classes. Without his instruction, this thesis could not have been completed. I would like to thank my committee members, Dr. Carl J. Lovely and Dr. Junha Jeon, for their support and advice. I would also like to thank other organic faculty members, Dr. Alejandro Bugarin, who have taught me a lot of chemistry. I would like to thank my group members Dr. Andra Corder, Diego Lopez, Mohammad Hossain, Pawan Thapa, Shakar Afzal, and Amanda Dark for their teamwork, support and knowledge sharing. I would like to thank Dr. Ching-Yuh Chen for giving me the opportunity to know what organic synthesis is. Without her enlightenment, I might not know how interesting. organic chemistry is. I would like to thank my family who have given me eternal support and love. They have given me the opportunity to come to the United States of America to pursue my higher education and know a variety of people who come from different countries.
    [Show full text]
  • REACTIONS of HALOCYCLOPROPANES. The
    This dissertation has been microfilmed exactly as received 69-11,652 HOUSER, Charles W., 1934- REACTIONS OF HALOCYCLOPROPANES. The Ohio State University, Ph.D., 1968 Chemistry, organic University Microfilms, Inc., Ann Arbor, Michigan REACTIONS OF HALOCYCLOPROPANES DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School o f The Ohio State U niversity By Charles W. Houser, B.A. ******** The Ohio State U niversity 1968 Approved hy /Adviser Department of Chemistry Dedicated to Jane and Brian i l ACKNOWLEDGMENTS The author wishes to express sincere appreciation to Professor Harold Shechter for the inception of this problem and for his helpful discussions throughout the course of this research. His editorial guidance during preparation of this manuscript is also gratefully acknowledged. National Science Foundation and Petroleum Research Fund are thanked for their financial assistance to this research. The author owes a special debt of gratitude to his wife, Jane, for her patience and encouragement during completion of this work. i i i VITA October 20, 1934 Born - Parkersburg, West Virginia 1954-1958 U. S. Marine Corps 1962 B.A., David Lipscomb College, Nashville, Tennessee 1962-1965 Teaching Assistant, The Ohio State University, Columbus, Ohio I965-I968 Research Associate, The Ohio State University, Columbus, Ohio iv CONTENTS Page ACKNOWLEDGMENTS.......................................................................................................... i i i VITA .........................................................................
    [Show full text]
  • Cyclopentane Synthesis
    Cyclopentane Synthesis Dan O’Malley Baran Group Meeting Cyclopentane Synthesis Group Meeting O'Malley 2/9/2005 This presentation is broken down into the following catagories. Some reactions either fit more than one Students of organic chemistry are taught a number of reactions for the synthesis of category or do not fit easily into any of them. Efforts have been made to place all such reactions in the cyclohexanes at a very early stage of their careers. Techniques for the creation of cyclopentanes, most appropriate category. however, are generally taught at a much later stage and are rarely given the same detailed treatment. This may be the result of the fact that there are no equivalents of reactions such as the Diels-Alder and I. General Information Robinson Annulation in terms of generality, extent of use, and historical importance. This may, in turn, II. Ionic Reactions be caused by the fact that the cyclopentane is an inherintly "umpoled" functionality, as illustrated below. III. Metal Mediated Reactions IV. Radical Reactions FG V. Pericyclic and Pseudo-pericyclic Reactions VI. Ring Expansion and Contraction Reactions I. General Information This situation is further exacerbated by the general lack of cheaply available cyclopentane compounds Baldwin's rules in the chiral pool; wheras a number of cyclohexane terpenes are readily available for elaboration, there Baldwin has divided ring closure reactions into those that are "favored" and those that are "disfavored". are no analogous cylcopentane natural products. Cyclopentanes are however, present in many Those that are disfavored are not always impossible, but are frequently much more difficult to effect.
    [Show full text]
  • Synthesis and Reactivity of Small Ring Bicyclic Compounds Raymond Lee Welch Iowa State University
    Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1969 Synthesis and reactivity of small ring bicyclic compounds Raymond Lee Welch Iowa State University Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Organic Chemistry Commons Recommended Citation Welch, Raymond Lee, "Synthesis and reactivity of small ring bicyclic compounds " (1969). Retrospective Theses and Dissertations. 3807. https://lib.dr.iastate.edu/rtd/3807 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. This dissertation has been microfilmed exactly as received 70-7767 WELCH, Raymond Lee, 1948- SYNTHESIS AND REACTIVITY OF SMALL RING BICYCLIC COMPOUNDS. Iowa State University, PhJD., 1969 Chemistry, organic University Microfilms, Inc., Ann Arbor, Michigan SYNTHESIS AND REACTIVITY OF SMALL RING BICYCLIC COMPOUNDS by Raymond Lee Welch A Dissertation Submitted to the Graduate Faculty in Partial Fulfillment of The Requirements for the Degree of DOCTOR OF PHILOSOPHY Major Subject: Organic Chemistry Approved : Signature was redacted for privacy. In Charge of Major Work Signature was redacted for privacy. Signature was redacted for privacy. Iowa State University Of Science and Technology
    [Show full text]
  • Table of Contents 1. Acyloin Condensation 1 2
    Contents |(vii) TABLE OF CONTENTS 1. Acyloin Condensation 1 2. Alder-Ene Reaction (Conia Reaction) 3 3. Alder-Rickert Reaction 5 4. Allan-Robinson Condensation 6 5. Aldol Condensation 8 6. Allylic Rearrangement 11 7. Amdori Glucosamine Rearrangement 14 8. Angeli-Remini Reaction 16 9. Anschutz Anthracene Synthesis 17 10. Appel Reaction 19 11. Arndt-Eistert Synthesis 21 12. Aston-Greenburg Rearrangement 24 13. Aza-Claisen Rearrangement 26 14. Baeyer Indole Synthesis 27 15. Baeyer Oxindole Synthesis 29 16. Baeyer Pyridine Synthesis 30 17. Baeyer-Villiger Oxidation 32 18. Baltz-Schiemann Reaction 34 19. Baker-Venkataraman Rearrangement 36 20. Bamberger Rearrangement 38 21. Barbier Reaction 40 22. Barton Reaction 42 23. Barton-Zard Pyrrole Synthesis 44 24. Bartoli Indole Synthesis 47 25. Baumann-Fromm Thiophene Synthesis 49 26. Beckmann Rearrangement 51 27. Benzidine Rearrangement 53 28. Benzilic Acid Rearrangement 56 29. Benzoin Condensation 58 30. Birch Reduction (Metal – Ammonia Reduction) 60 31. Bischler-Napieralski Reaction 63 32. Blaise Reaction 66 33. Bohlmann-Rahtz Pyridine Synthesis 68 (vii) (viii)| Contents 34. Bodroux Amide Synthesis 70 35. Bouveault Aldehydes Synthesis 72 36. Bouveault-Blanc Reduction 74 37. Bruckner Isoquinoline Synthesis 77 38. Bucherer Carbazole Synthesis 80 39. Cadiot-Chodkiewicz Coupling 82 40. Cannizzaro Reaction 84 41. Carbylamine Reaction 87 42. Carroll Rearrangement 89 43. Chichibabin Amination Reaction 91 44. Chichibabin Pyridine Synthesis 93 45. Chugaev Elimination 96 46. Claisen Condensation 98 47. Claisen Rearrangement 101 48. Claisen-Schimdt Reaction 104 49. Clemmensen Reduction 107 50. Combes Quinoline Synthesis 110 51. Cope Elimination 113 52. Cope, Oxy-Cope, and Anionic Oxy-Cope Rearrangements 115 53.
    [Show full text]
  • Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Gen- Erated from Inosose 2-O-Mesylates
    SYNLETT0936-52141437-2096 © Georg Thieme Verlag Stuttgart · New York 2015, 26, 111–115 111 letter Syn lett K. P. Stockton et al. Letter Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Gen- erated from Inosose 2-O-Mesylates Kieran P. Stockton O O O RO Stephen A. Glover RO OH RO ROH RO Ben W. Greatrex* 1. MsCl, Et3N RO OR 2. Et N, ROH RO OR School of Science and Technology, University of New England, 3 RO OR Armidale, 2351, Australia OR OR OR [email protected] up to 64% yield tolerant of stereochemistry Received: 07.09.2014 some addition products,13 trapping reactions,14 as well as Accepted after revision: 13.10.2014 reaction rates for alcoholysis reactions15 have been used as Published online: 14.11.2014 DOI: 10.1055/s-0034-1379490; Art ID: st-2014-d0743-l evidence for the oxyallyl intermediate 3, while stereospecif- ic examples of the rearrangement provide evidence for di- Abstract Protected inosose 2-O-mesylates generate oxyallyl systems rect synchronous cyclopropanone formation.9,16 by elimination of the mesylate group after enolization. The reaction is promoted by weak bases such as triethylamine and azide, and the oxy- O O O allyl systems are then trapped by nucleophilic alcohols or azide. Compu- tations using DFT/B3LYP confirm that the singlet planar oxyallyl is stabi- Br RONa RONa OR lized by the exocyclic alkoxy group. ROH Key words nucleophilic addition, carbocycle, carbohydrates, rear- rangement, carbocation 1 2 4 The oxyallyl system is a transient reactive group often – O used in [4+3]-cycloaddition reactions to form seven-mem- O OR bered and bicyclic structures.1–3 Macmillan et al.
    [Show full text]
  • Acetylene in Organic Synthesis: Recent Progress and New Uses
    Review Acetylene in Organic Synthesis: Recent Progress and New Uses Vladimir V. Voronin 1, Maria S. Ledovskaya 1, Alexander S. Bogachenkov 1, Konstantin S. Rodygin 1 and Valentine P. Ananikov 1,2,* 1 Institute of Chemistry, Saint Petersburg State University, Universitetsky prospect 26, Peterhof 198504, Russia; [email protected] (V.V.V.); [email protected] (M.S.L.); [email protected] (A.S.B.); [email protected] (K.S.R.) 2 N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky prospect 47, Moscow 119991, Russia * Correspondence: [email protected] Received: 16 August 2018; Accepted: 17 September 2018; Published: 24 September 2018 Abstract: Recent progress in the leading synthetic applications of acetylene is discussed from the prospect of rapid development and novel opportunities. A diversity of reactions involving the acetylene molecule to carry out vinylation processes, cross-coupling reactions, synthesis of substituted alkynes, preparation of heterocycles and the construction of a number of functionalized molecules with different levels of molecular complexity were recently studied. Of particular importance is the utilization of acetylene in the synthesis of pharmaceutical substances and drugs. The increasing interest in acetylene and its involvement in organic transformations highlights a fascinating renaissance of this simplest alkyne molecule. Keywords: acetylene; vinylation; cross-coupling; addition reactions; drugs; pharmaceutical substances; biologically active molecule; monomers; polymers 1. Introduction Since the discovery of acetylene, new areas of acetylene chemistry have been continuously developed. The rich scope of chemical transformations available for a C≡C triple bond can be exemplified by coupling [1–5] and addition reactions [6,7].
    [Show full text]
  • FIVE-MEMBERED RING FORMATION 138 5 Membered Rings
    FIVE-MEMBERED RING FORMATION 138 5 Membered Rings HO O CO2H CO2H HO OH HO OH PGF2a PGE2 Me H Me Me Me Me Me Me Me Hirsutene Modhephane Isocumene 1. Intramolecular SN2 Reactions 2. Intramolecular Aldol Condensation and Michael Addition 3. Intramolecular Wittig Olefination 4. Ring Expansion and Contraction Reactions a. 3 ® 5 b. 4 ® 5 c. 6 ® 5 5. 1,3-Dipolar additions 6. Nazarov Cyclization 7. Arene-Olefin Photocyclization 8. Radical Cyclizations 9. Others Synthesis 1973, 397; ACIEE 1982, 21 , 480; Intramolecular SN2 Reaction 5-exo-tet: favored O LDA O JCSCC 1973, 233 Br O O O CO2Me CO2Me Br CN CN OH JACS 1974, 96 , 5268 O FIVE-MEMBERED RING FORMATION 139 O Cl O JACS 1979, 101 , 5081 RO2C CO R RO2C Cl 2 CO2R O O NaH, DMSO JCSCC 1979, 817 TsO Intramolecular Aldol Condensation 5-exo-trig: favored intramolecular aldol condensation of 1,4-diketones O O R R O R' R' O O CH3 CH3 TL 1982, O 29, 2237 CH3 CH3 Br Br O NaOMe, MeOH O JACS 1980, 102 , 4262 O CO2Me CO2Me O O NaOH JOC 1983, O O 48 , 1217 O Intramolecular Michael Addition 5-exo-tet: favored Organic Reactions 1995, 47, 315-552 O O JACS 1979, 101 , 7107 O MeO2C O FIVE-MEMBERED RING FORMATION 140 Intramolecular Wittig Olefination Tetrahedron 1980, 36, 1717 O O - O 1) (MeO) P(O)CH P(OMe)2 2 2 O 2) Collins O C5H11 THPO OTHP C5H11 THPO OTHP JOC 1981, 46 , 1954 O CO2H base C5H11 THPO OTHP C5H11 HO OH Ring Expansion Reactions - 3 ® 5: Vinyl Cyclopropane Rearrangement Organic Reactions 1985, 33, 247.
    [Show full text]
  • HFO-1234Yf As a CF3-Building Block : Synthesis and Chemistry of CF3-Ynones.', European Journal of Organic Chemistry., 2020 (39)
    Durham Research Online Deposited in DRO: 23 October 2020 Version of attached le: Published Version Peer-review status of attached le: Peer-reviewed Citation for published item: Murray, Ben J. and Marsh, Thomas G. F. and Yut, Dmitri S. and Fox, Mark A. and Harsanyi, Antal and Boulton, Lee T. and Sandford, Graham (2020) 'HFO-1234yf as a CF3-building block : synthesis and chemistry of CF3-ynones.', European journal of organic chemistry., 2020 (39). pp. 6236-6244. Further information on publisher's website: https://doi.org/10.1002/ejoc.202001071 Publisher's copyright statement: c 2020 The Authors published by WileyVCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. Additional information: Use policy The full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that: • a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders. Please consult the full DRO policy for further details. Durham University Library, Stockton Road, Durham DH1 3LY, United Kingdom Tel : +44 (0)191 334 3042 | Fax : +44 (0)191 334 2971 https://dro.dur.ac.uk EurJOC Full Paper European Journal of Organic Chemistry doi.org/10.1002/ejoc.202001071 Fluorine Chemistry HFO-1234yf as a CF3-Building Block: Synthesis and Chemistry of CF3-Ynones Ben J.
    [Show full text]
  • Modern Alkyne Chemistry Related Titles
    Edited by Barry M. Trost and Chao-Jun Li Modern Alkyne Chemistry Related Titles Georgakilas, V. (ed.) Behr, A., Neubert, P. Transition-Metal-Mediated Applied Homogeneous Aromatic Ring Construction Catalysis 2013 2012 Print ISBN: 978-1-118-14892-1 Print ISBN: 978-3-527-32641-9 (Also available in a variety of digital formats) Bullock, R.M. (ed.) Hashmi, A.S., Toste, F.D. (eds.) Catalysis without Precious Modern Gold Catalyzed Metals Synthesis 2010 2012 Print ISBN: 978-3-527-32354-8 Print ISBN: 978-3-527-31952-7 (Also available in a variety of digital formats) (Also available in a variety of digital formats) Nugent, T.C. (ed.) RiosTorres,R.(ed.) Chiral Amine Synthesis The Pauson-Khand Reaction - Methods, Developments and Scope, Variations and Applications Applications 2010 Print ISBN: 978-3-527-32509-2 2012 Print ISBN: 978-0-470-97076-8 (Also available in a variety of digital formats) (Also available in a variety of digital formats) Edited by Barry M. Trost and Chao-Jun Li Modern Alkyne Chemistry Catalytic and Atom-Economic Transformations The Editors All books published by Wiley-VCH are carefully produced. Nevertheless, authors, Prof. Dr. Barry M. Trost editors, and publisher do not warrant the Stanford University information contained in these books, Department of Chemistry including this book, to be free of errors. 330 Roth Way Readers are advised to keep in mind that Stanford statements, data, illustrations, procedural CA 94305-5080 details or other items may inadvertently USA be inaccurate. Prof. Dr. Chao-Jun Li Library of Congress Card No.: applied for McGill University Department of Chemistry British Library Cataloguing-in-Publication 801 Sherbrook Street West Data Montreal A catalogue record for this book is Quebec H3A 0B8 available from the British Library.
    [Show full text]
  • United States Patent (19) 11 Patent Number: 5,410,094 Babler 45 Date of Patent: Apr
    US005410094A United States Patent (19) 11 Patent Number: 5,410,094 Babler 45 Date of Patent: Apr. 25, 1995 54 TERTARY ALKYNOLS 2R,4R,8R-a-Tocopherol Vitamin E. Construction of 75) Inventor: James H. Babler, Chicago, Ill. Chiral Chromans from an Optically Active, Nonaromatic Precursor, Journal of the American Chemical Society, 73 Assignee: Loyola University of Chicago, 1979, pp. 6710-6716. Chicago, Ill. Chan, et al., Synthesis of 2R,4R, 8R-a-Tocopheryl Ace 21 Appl. No.: 255,369 tate Vitamin E Acetate Using 3,3 Sigmatropic Rear 22 Filed: Jun. 8, 1994 rangement, The Journal of Organic Chemistry, vol. 43, No. 18, 1978, pp. 3435-3440. Russell, A. and Kenyon, R. L., Pseudoionone, Organic Related U.S. Application Data Syntheses Collective vol. 3, pp. 747-750 1955. 62) Division of Ser. No. 976,219, Nov. 25, 1992, Pat. No. Haynes, L.J. and Jones, E. R. H., Unsaturated Lactones, 5,349,071. Part I J. Chem. Soc., 1946, pp. 954-957. 51 Int. Cl.' .................... C07C33/042; CO7C 43/14; Sato, K., et al., Japanese Patent Application 26,656('63) C07C 43/166; C07C 43/178 6,10,14-Trimethylpentadeca-6-en-yn-2-ol, Chem. (52) U.S.C. .................................... 568/662; 556/449; Abstr., 1964, p. 6746(e). 568/675; 568/855 Acetylene-Alcohol, Compendium of Organic Synthetic 58) Field of Search ....................... 568/855, 675, 662; Methods, vol. 2, Section 302, pp. 218–220 1974. 556/449 Acetylene-Alcohol, Compendium of Organic Synthetic 56 References Cited Methods, vol. 3, Section 302, p. 337 1977. U.S. PATENT DOCUMENTS (List continued on next page.) 2,529,498 11/1950 Isler ....................................
    [Show full text]