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From the Activation of Tetraphosphorus to the Chemistry of Diphosphorus and Beyond by Daniel Tofan B.S., California Institute of Technology (2008) Submitted to the Department of Chemistry in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry at the MASSACHUSETTS INSTITUTE OF TECHNOLOGY June 2013 © Massachusetts Institute of Technology 2013. All rights reserved. Author.......................................................................... Department of Chemistry May 28, 2013 Certified by. Christopher C. Cummins Professor of Chemistry Thesis Supervisor Accepted by . Robert W. Field Chairman, Department Committee on Graduate Theses 2 This Doctoral Thesis has been examined by a Committee of the Department of Chemistry as follows: Professor Mircea Dinca..................................................................˘ Assistant Professor of Chemistry Chairman Professor Christopher C. Cummins . Professor of Chemistry Thesis Supervisor Professor Elizabeth M. Nolan . Pfizer Laubach Career Development Assistant Professor of Chemistry Committee Member 3 4 From the Activation of Tetraphosphorus to the Chemistry of Diphosphorus and Beyond by Daniel Tofan Submitted to the Department of Chemistry on May 28, 2013, in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry Abstract − t The niobium–phosphorus triple bond in [P≡Nb(N[Np]Ar)3] (Np = CH2 Bu; Ar = 3,5-Me2C6H3) has produced the first case of P4 activation by a metal–ligand multiple bond. Treatment of P4 with the sodium salt of the niobium phosphide complex in weakly-coordinating solvents led to the for- mation of the C3-symmetric cyclo-P3 anion, while in THF, it led to the formation of the cyclo-P5 4 − anion [(Ar[Np]N)(h -P5)Nb(N[Np]Ar)2] . The latter represents a rare example of a substituted pentaphospha-cyclopentadienyl ligand and may be interpreted as the product of trapping an inter- 5 mediate h -P5 structure through the migration of one anilide ligand. A search for methods of activating P4 that avoid tedious metal-mediated steps led to the dis- covery of an incredibly simple procedure involving only commercial reagents. Irradiation of so- lutions containing P4 and readily available 1,3-dienes produced bicyclic organic diphosphanes in an atom-economical, one-step protocol. Use of 2,3-dimethylbutadiene allowed the isolation of the bicyclic diphosphane P2(C6H10)2 in gram-quantities, but other dienes such as 1,3-butadiene, isoprene, 1,3-pentadiene, and 1,3-cyclohexadiene also provided evidence for incorporation of P2 units via double Diels–Alder reactions. Theoretical investigations provided support for the forma- tion of P2 molecules from photo-excited P4. Investigations into the physical and chemical characteristics of P2(C6H10)2 uncovered an un- precedented stability towards cleavage of the P–P bond relative to other diphosphanes. P2(C6H10)2 exhibits a flexible, yet robust bicyclic framework containing lone pairs disposed at an angle of ca. 45◦, and proved to be ideally suited to form multiple bridges between two metal centers. Dinuclear complexes containing tetrahedral, zero-valent group 10 metals bridged by three diphos- phane ligands were investigated in detail. These contain D3h-symmetric fM2P6g barrelene cages with metal–metal distances of 4 A,˚ and exhibited substitution reactions where the cages remain intact. Alternatively, diphosphane P2(C6H10)2 allowed for unprecedented selectivity towards func- tionalization of a single phosphorus lone pair. Additional functionalization proceeds at a signifi- cantly slower rate, thus enabling the selective isolation of various phosphoranes (EP2(C6H10)2 and E2P2(C6H10)2; E = O, S, N-R). Metalation reactions with the bulky diiminodiphosphorane ligand (MesN)2P2(C6H10)2 allowed for multiple metal complexes, showing that such ligands provide an attractive pre-organized binding pocket for transition metals, as well as post-transition metals. Thesis Supervisor: Christopher C. Cummins Title: Professor of Chemistry ii Acknowledgments The thesis would not have been possible without the assistance, guidance, and support of many people. While there are surely many more than those listed here, I would like to acknowledge several individuals for their help throughout my path here. Kit, my advisor and mentor has been the person with the greatest impact on my development as an academic professional. From the first meeting I had with him at MIT, I have greatly admired his enthusiasm on making an impact on the world by studying fundamental questions posed by Nature. By joining his group five years ago, I got the rare opportunity to work on some very fundamental chemical transformations. I am immensely grateful for the freedom he has allowed me in pursuing various chemical leads. In exchange, Kit has pushed me to my limits. His demanding style and insatiable curiosity have made me a more rigorous professional. I truly appreciate the amount of patience he has shown towards me during some of the hardest steps in my development as an individual during graduate school. Although at times I did not find his methods to be optimal, I really value the positive intentions with which he has guided his interactions with me. Although the rest of the Cummins Group has changed completely during my time at MIT, I found it to be a continuous source of cooperation and positive interaction that allowed me to better myself as an individual. Among fellow graduate students, Curley has probably had the largest impact on my development as a chemist. Although I overlapped with him for only a year, he has been the most enthusiastic member to take the time and share his knowledge about experimental aspects of chemistry — which perhaps back then, I did not get to appreciate sufficiently. My research has been in many aspects a continuation of the work done by Nick, and as a result I got the opportunity to learn from him many tricks on how to perform difficult reactions. Brandi has been a source of inspiration for efficiency and result targetting. Anthony has been a model for working in a cooperative environment. Although the professional growth has been a large aspect of graduate school, the personal development has proven to be the field where graduate school has had the largest impact. It would be truly impossible for me to accurately put in words the impact that Alexandra has had on many sides of my experiences at MIT. Jared has become my personal model for rational development of personal character and maturation of interpersonal skills. Christian, Rankin, and Diego have been the best colleagues and friends for learning to take a break from the mental strain of working long hours. Having the opportunity to mentor several undergrads — Katie, T.J., Evan, and Tawanda — iii has taught me the invaluable lesson of patience. Mentoring Jens, Manuel, Carolin, Mona, Chao and other exchange students has helped me learn how to communicate more efficiently my ideas to individuals that have a very different background. Additional members of the group, including Manis, Glen, Arfox, Ivo, Heather, and Montag shared their expertise in my first years at MIT, while in the later years, other members, including Ioana, Julia, Matt, Runyu, or Nazario, were very helpful in providing feedback when working on manuscripts. Collaborations with individuals outside of the group helped me learn some techniques that I had limited experience in, whether it was X-ray refinement methods from Peter Muller,¨ Mike Takase, Nadia Marino; NMR spectroscopy from Jeff Simpson; computations from Manuel Tem- prado Lee-Ping Wang; or other experimental techniques from Carl Hoff and Yuan Zhang. Time spent with Markrete Krikorian and Peter Curtin offered me memorable experiences outside the lab during my time at MIT. Several people had a significant impact in helping me walk on the path to MIT. Maria Cindrea, Daniela Teodorescu, Maria Metea, Sergiu Ungureanu, Alex Hening, and Gino Giri had a large influence in shaping my interest for science. At Caltech, John Bercaw and Theodor Agapie shared with me some of their vast knowledge and offered me the chance for the first time to really apply my chemical curiosity into scientific inquiries. Lastly, my family has proven to be the one constant source of support and positive energy throughout any difficulties I encountered on my path here. I am dedicating my work to them: Vasile, Lica, and Iulian. iv Table of Contents 1 Tetraphosphorus Activation at a Metal–Phosphorus Triple Bond of a Niobium Trisanilide Platform 1 1.1 Background: Activation of P4 with Transition Metal Complexes.........5 1.2 A Niobium cyclo-P3 Complex from the Activation of P4 .............5 1.3 A Niobium cyclo-P5 Complex from the Activation of P4 .............9 1.4 Activation of P4 and AsP3 with Related Niobium Trisanilide Platforms...... 12 1.5 Factors for Divergent Pathways in P4 Activation.................. 14 1.6 Computational Insights into the Activation of P4 ................. 17 1.7 Anionic Niobium Complexes as Sources for the Generation of Molecular Phosphorus 19 1.8 Concluding Remarks................................ 19 1.9 Experimental Details................................ 20 1.10 References...................................... 28 2 Photolysis of Tetraphosphorus Leading to the Incorporation of Diphosphorus Units into Organic Molecules 31 2.1 Background: Search for a Direct Route to Diphosphorus Units.......... 35 2.2 Trapping of P2 Units from the Photolysis of P4 with 1,3-Dienes.......... 36 2.3 Characteristics of Bicyclic Diphosphanes
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  • GLOSSARY of CLASS NAMES of ORGANIC COMPOUNDS and REACTIVE INTERMEDIATES BASED on STRUCTURE (IUPAC Recommendations 1995)

    GLOSSARY of CLASS NAMES of ORGANIC COMPOUNDS and REACTIVE INTERMEDIATES BASED on STRUCTURE (IUPAC Recommendations 1995)

    Pure &App/. Chem., Vol. 67, Nos 819, pp. 1307-1375, 1995. Printed in Great Britain. (B 1995 IUPAC INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY ORGANIC CHEMISTRY DMSION COMMISSION ON NOMENCLATURE OF ORGANIC CHEMISTRY (III. 1) COMMISSION ON PHYSICAL ORGANIC CHEMISTRY (III.2) GLOSSARY OF CLASS NAMES OF ORGANIC COMPOUNDS AND REACTIVE INTERMEDIATES BASED ON STRUCTURE (IUPAC Recommendations 1995) Prepared for publication by G.P. MOSS, P.A.S. SMITH and D. TAVERNIER Cornpodtion of the ZZZ.1 & 111.2 Working Party (1980-1994): H.J.T. Bos, A.J. Boulton, E.W. Godly, P. Griinanger, A.D. McNaught, G.P. Moss, R. PanicO, J. Rigaudy, P.A.S. Smith (Conwnorfiom ZZZ, I), J.H. Stocker, D. Tavernier, R.A.Y. Jones, J. March, J.M. McBnde, P. Miiller (Conwnorfim 111.2). Membership of the Commission on Nomenclature of Organic Chemistry during the preparation of this document (1980-1994) was as follows: Titular Members: 0. Achmatowicz (Poland) 1979-1987; H. J. T. Bos (Netherlands) 1987- , Vice-Chairman, 1991- ; J. R. Bull (Republic of South Africa) 1987-1993; H. A. Favre (Canada) 1989- , Chairman, 1991- ; P. M. Giles, Jr. (USA) 1989- ; E. W. Godly (UK) 1987-1993. Secretary, 1989-1993 ; D. Hellwinkel (Federal Republic of Germany) 1979-1987, Vice- Chairman, 1981-1987; B. J. Herold (Portugal) 1994- ; K. Hirayama (Japan) 1975-1983; M. V. KisakUrck (Switizrland) 1994- ; A. D. McNaught (UK) 1979-1987; G. P. Moss (UK) 1977- 1987, Chairinan, 1981- 1987, Vice-Chainnun, 1979-1981; R. Panico (Francc) 1981-1991, Vice- Chairman, 1989-1991; W. H. Powell (USA) Secretary, 1979-1989; J.