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STUDIES I3ST the AZULBKS AETD TBQPQLQUB 3BBIE3« a (Thesis Fo STUDIES I3ST THE AZULBKS AETD TBQPQLQUB 3BBIE3« A (Thesis for the degree of Ph.D. AETDBBff B. SOMERVILLE, B.So., A.B.I.Q. Glasgow University September, 1949, ProQuest Number: 13870200 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. uest ProQuest 13870200 Published by ProQuest LLC(2019). Copyright of the Dissertation is held by the Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States Code Microform Edition © ProQuest LLC. ProQuest LLC. 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, Ml 4 8 1 0 6 - 1346 Acknowledgments. The author wishes to thank Professor J.W. Gook, D.Sc., Jf*.R.S. for his constant help and invariable encouragement throughout this work. Microanalyses were carried out by Mr. J.M.L. Gameron and Miss R.H. Kennaway. for permission to work in the laboratories of the EidgenSssische fechnische Hochschule, Zllrich, from May to September 1948, the author is indebted to Professor L. Ruzicka; and for valuable advioe during this period, to Professor P.A. Plattner and Dr. A. Etlrst. Mioroanalyses in this section were carried out by Herr W. Manser. Eor a Maintenance Allowance during 1945-46 the author is indebted to the Department of Scientific and Industrial Research, and for a grant towards expenses in Ztlrich to the University of Glasgow. 0 o n t ents. P a rt I Azulenes* 1 Experimental* 58 B ibliography* 71 P a rt I I Tropolones* 74 Exp eriment al* 95 References: 113. Part I - Azulenes. Summary. A new synthesis of azulene is described. Suberone is condensed with diethyl suooinate, the product (XXIII) oyclised and the resulting keto-ester hydrolysed and deoar- boxylated to 1-keto-ootahydroazulene (XXIV). This has been reduced by aluminium isopropoxide to the corresponding oarbinol, and by the Clemmensen method, after hydrogenation of the double bond, to deoahydroazulene. These products have been dehydrogenated to give azulene in small yields. The synthesis of 1-phenylazolene from the ketone XXIV was attempted, but has not been suooessful. A sim ilar condensation of 2:3-benzosuberone with diethyl suooinate followed by oyclisation etc. led to 1 - ke t oh ex ahy d rob enz az ul ene (XXXII) which has been reduced by various means, but dehydrogenation of the reduction products to 4:5-benzazulene has not been accomplished. 2-M ethyl- 6-oarb ethoxy azulene has been prepared by treatment of 2-methyl indane with diazoacetio ester and dehydrogenation of the product. This has been hydrolysed to the free acid, ammonolysed to the amide, and reduoed with lithium aluminium hydride to 2-m ethyl - 6-hydroxym ethyl- azulene. Attempts at Hofmann degradation or lithium aluminium hydride reduotion of the amide, in order to obtain amines, were unsuccessful. Early work. The name azulene was first given to the blue colour­ e d ) ing matter of oamomile oil , which has been used as a soothing agent for burns and skin irritations for a very long time. About 50 other essential oils either possess such colours or can give rise to them by treatment with acids or by dehydrogenation. Investigation of these colouring matters made little progress until Shemda^s discovery in 1915^ that they could be extracted from the essential oils with strong mineral acids, such as 80$ phosphoric acid. A red complex is formed which dissociates on dilution with water, and the colouring matter can then be extracted with hydrocarbon solvents. In this way Sherndal obtained homogeneous m aterials, forming black picrates. Their formula was indicating re­ lationship to the sesquiterpenes. By 1936 a large number of azulenes had been isolated in this way from different sources, but on systematic com­ parison the number of distinct individuals was found to be only five - chan* , - from camomile oil, S -gua;}- from su lp h u r dehydrogenation of guajol, from selenium dehydro­ genation of guajol, lactar- from the fungus lactarius ( 4 ) , ( 6 ) delioiosus 1 . and vetivazulene from vetiver oil These are known as the "natural" azulenes, though in fact they are probably not present in the plant as such, but are formed during the extraction of the essential oil. They are all isomeric, having the formula 0ar l y work shov/ed that they contained two rings and five double bonds. Oxidation gave fragments too small to be of any use and investigation was therefore directed towards their hydro­ genation products and towards the parent sesquiterpenes. S tr u c tu r e . In 1936 Pfan and Plattner^^ elucidated the structure of the azulenes through a study of the related sesquiterpene ketones extracted with Girard*s reagent from vetiver oil^9* '^ These ketones were converted to a mixture of semicarbazones which could be separated by crystallisation into a d- and an 1 -fraction, and the pure ketones regenerated from these were designated and /3-vetivone respectively. These ketones have the formula and molecular refraction measurement showed that they are bioyclic and one of their two double bonds is conjugated with the keto group. Reduction of the keto group to the oarbinol, followed by dehydration and de­ hydrogenation with Se or S led to a mixture of hydrocarbons* an azulene vetivazulene, c 1 gs1Q» eudalene and 1*5-dimethyl- 7-isopropyl naphthalene, the formation of the latter two compounds showing that the rings are fused ortho. The -CH = CH - 00 - system of ^-vetivone was now reduced to -OHg - CH2 - GHOH-, and the resalting dihydro— (3-vetivol when sabjected to ozonisation split off a molecale of acetone, indicating the presence of an isopropylidene groap, ti> give a hydroxy ketone I, Tahich coaid be dehydrated to the ansatarated ketone II. This in tarn was farther redaced, dehydrated and dehydrogenated to an azalene /,—cwx z'— CH* —-Cll I II CROtf CH-oH Cu Cn I O3 K|| Chl —H»p i - * Ck Hh C«L I 1 \ _ H|0 azalene C12H12 - C o I + M«fcCo I — CM, dih y d ro - p -v e tiv o l II If the redaction of (2-vetivone to dihydro-vetivol was carried oat with soaiam in alcohol, then the sabseqaent degradation prodacts, inclading the ansatarated ketone II, were foand to be optioally active; whereas if the redaction were carried oat oatalytioally to give a stereoohemioally pare dihydro-P-vetivol, then the sabseqaent prodacts were foand to be inactive, yet gave no m.p. depression with the other series. These inactive compoands were assamed to be internally compensated, from which it follows that the system 5 . \ C \ C -C I CO -- IK c ./ mast be present in di hydro-( 2- vetivone, the two rings being unequal in size, thus giving the molecule an axis of sym­ metry. Sinoe dihydro-p- vetivone forms a dibenzylidene derivative it can therefore be formulated in aocordance with the isoprene rule as III, the corresponding structure for p-vetivone being IY. t=o I I I XT These formulae explain the facts if it is assumed (a^ that the rings are fused in a cis position, and (b) that oatalytio hydrogenation of IY direots the Me on C1Q cis to the Me on 0^, resulting in an inactive compound (V), while Sa/EtOS produces the opposite result (YI), at any rate in part H h ft* ru T H Thus the derivatives of Y are inactive, and those of YI active. Dehydration of the hydroxy ketone YII oan take place in two directions, giving equal amounts of VIII and IX, 6 . OH 0=? VII VIII IX which, if the meso form is used, are optical antipodes so that the product is a racemate of two active forms, where­ as when the asymmetric form of VII is dehydrated, the products are both active, but not enantiomorphous. On this basis, then, the azulene woul<3- 130 ■*» an^ vetivazulene XI, these being the normal dehydrogenation products, the naphthalenes being produced by rearrangement. X This cyolopentano-cycloheptane skeleton was now confirmed by oxidative degradation. The tetrahydro-^ - vetivone XII was oxidised to the dicarboxylic acid XIII, which could then be ring closed to the apo-ketone XIV followed by dehydrogenation to the known indanol XV, OH XIII XIV XV thus confirming the presence of a 7-membered ring in the original* The presence of a 5-membered ring was similarly- shown by oxidation of the ketone VIII, after hydrogenation of the double bond, to a dicarboxylic acid XVI which ooald not be ring closed to an apo-ketone. 0=< HO,C V III XVI final confirmation was obtained by synthesis of ( 8) vetivazulene A similar investigation of the sesquiterpene alcohol guajol led to the establishment of the structure XVII, and the 5 -gua;jazalene formed from it by S dehydrogenation was shown to be XVIII, while Se-gaa^azalene is considered to be XIX, formed by m ig ra tio n o f the 1-Me group to th e 2 -p o s it ion under the influence of the higher temperature of the Se (11,12,13,14,15) dehydrogenation XVII XVIII XIX In addition to lac tar azulene, the fungus lactarius delioiosis L. contains an interesting violet pigment, lac taro violin, which has been shown to be an isopropenyl azalene-aldehyde (33,34,59,60) The parent straotare of the azalenes then, is the hi oyolo (0:3;5)-deoapentaene skeleton. This compound is now oailed rtazulene” and is numbered thus: Yetivazulene is therefore 4: 8 - dimethyl-2-iso propyl - azulene, and S-guajazulene is 1j4-dimethyl-7-isopropylazulene.
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