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Extra info for Aliphatic, Alicyclic and Saturated Heterocyclic Chemistry Volume 1 Part 1 a review of the literature published during 1970 and 1971
Studies of C,, and CIS Cecropia juvenile hormone necessitated a stereospecific synthesis of the heptenol (241), which was preparedlS2as shown. Conversion of the (241) phosphonium salt derived from (241) into the trisubstituted olefin (242) uses another stereospecific reaction, the addition of formaldehyde to the boxidoylide (243). Olefin (242) is converted in several steps into (&)XI, e CHzOTHP A. m P P h 3 I' 'f' CHO (243) THP = tetrahydropyranyl &&zo fOTHP (244) (242) 176 177 178 180 lS1 R. A .
P. E. Peterson, R. J. Bopp, and M. A. Ajo, J . Amer. Chem. ,1970,92, 2834. 1° In the presence of superacids, alkynes generate vinyl cations which are trapped by carbon monoxide. r. tube, gave (85), (86), and (87) (Scheme 5); (85) was explained by attack of adventitious water. Curiously, the stereochemistry of (86) implies attack of carbon monoxide upon Me---Me + Me \ c-c / / \ H Me OH2 HZO + Me \ + C=C-Me+ / H 1 MeCH,CMe I1 lC0 Me +OH H (85) iH+ \ / c=c / \ + CH=C / \ Me Me CO c o \ + / C=CMe, H + co Me (86) Scheme 5 the more hindered side of the (presumably linear) vinyl cation intermediate.
Garrard, and P. Chamberlain, Canad. J . Chem.. 1971, 49, 1099. 32 Aliphatic, Alicyclic, and Saturated Heterocyclic Chemistry obtained from decomposition of the diazoketone, implying a common intermediate ketocarbene for both reactions. 96 R? ,R2 (129) (128) An attempt to convert the aldehyde (130) into the corresponding ester (131) by the method of Coreyg7gave, in addition, the ester (132) and its transformation products. looFurther study has indicated that acetylenes O5 J. Ciabattoni, R. A. Campbell, C.
Aliphatic, Alicyclic and Saturated Heterocyclic Chemistry Volume 1 Part 1 a review of the literature published during 1970 and 1971