By M A McKervey, Chemical Society
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Extra resources for Alicyclic chemistry. Vol. 6 : a review of the literature published during 1976
Acta, 1976, 59, 475. B. H. Bakker, H. Steinberg, and Th. J. de Boer, Rec. Trau. , 1976,95,274. G . F. Koser and J. N. Faircloth, J . Org. , 1976,41, 583. G. Boche, D. -U. Wagner, J . Amer. Chem. ,1976,98,2668. I. 0. Shapiro, T. V. Leonova, Yu. I. Ranneva, Yu. S. Snagovskii, A. I. Shatenshtein, and Yu. S. Shabarov, Doklady Akad. , 1976,228,1357 (Chem. , 1976,85,123068); T. V. Leonova, I. Shapiro, Yu. I. Ranneva, 0. A. Subbotin, R. V. Kudryavtsev, Yu. S. Shabarov, and A. I. Shatenshtein, Zhur. org.
This behaviour is most compatible with the concerted addition of a RCF,CF,SiF, (68) R = H or C1 -+ RCF,eF (69) singlet species. "' At the wavelengths used, methylene is produced as a 0 (70) D. Seyferth and D. Dagani, J . , 1976,104, 145. l o 'C. W. Jefford, A. Delay, T. W. Wallace, and U. Burger, H e h . Chim. Acta, 1976, 59, 2355: C. W. Jefford, J. Mareda. -C. E. Gehret, nT. Kabengele, W. D. Graham, and U. Burger. J . Amer. Chem. , 197698, lob 2585. R. A. Moss and J. K. S. Chem. , 1976,950. lo' R .
S . Bien, A. Gillon, and S . S. Perkin I, 1976,489. W. Fischer, C. A. Grob, and H. Katayama, Helv. Chim. Acta, 1976,59, 1953. 123The addition of carbene (90; n = 2) to the terminal double bond (path a)to give the bicycle(91; n = 2) is the exclusive route adopted in (89:R' = R2 = H, n = 2) and the major (44 %) process in (89; R' = Ra = Me, n = 2). In this latter case Wolff rearrangement of carbene (90;R'= R2 = Me, n = 2) to (92; R' = R2 = Me, n = 2) (path b) also occurs and (94; R' = R2 = Me, n = 2) is obtained in 37% yield.
Alicyclic chemistry. Vol. 6 : a review of the literature published during 1976 by M A McKervey, Chemical Society