By M A McKervey, Chemical Society
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Extra info for Alicyclic chemistry. Vol. 6 : a review of the literature published during 1976
F. Rupert and J. D. S. Chem. , 1976,976; J. F. Rupert, M. A. Avery, and J. D. , p. 978. R. H. Rynbrandt, F. E. Dutton, and C. G. Chidester, J Arner. C h m . , 1976,98, 4483. 44 dNHcoM gNHC Alicyclic Chemistry ~ COMe (1 75) allylic cation (175) and cyclization to afford the observed p r o d ~ c t . ’” Apart from its use as a synthetic rnethod,lg’ the silver-ion-assisted solvolysis of gem-dihalogenocyclopropanes has received further detailed scrutiny. The solvolyses of 9,9-dibromobicyclo[6,1,O]-nonane and -non-4-ene both show both first- and second-order dependence on silver(r) ion.
However, in more severely strained cases, the initial formation of a transoid bridgehead olefin is not favoured and, for compound (180) at least,lga &+J -(Q-J-(+& ( 179) OH OH 37 % OH Reagent: i, AgC10,-Me,CO-H,O 9% Scheme 21 193 Y. Bessi6re and M. Schlosser, Helv. Chim. Acta, 1976, 59, 969. (c)C. B. Reese and A. C. Risius, TetrahedronLetters, 1976,4847; (b) P. Lu,J . Amer. Chem. , 1976,98, 6752. Alicyclic Chemistry 46 products the principal products arise by a solvolysis path in which the three-membered ring is initially retained.
1976,54, 1197. M. M. Gol'din, A. I. Dyachenko, and L. G. Feoktistov, Izvest. Akad. , Ser. , 1975,2605 (Chem. , 1976,84, 51 423). S . Farid and K. A. S. Chem. , 1976, 564. C. W. Jefford and C. G. Rimbault, Tetrahedron Letters, 1976,2479. A. R. Allan and M. S. Baird, Tetrahedron Letters, 1976, 3831. -L. Burgot, J. Masson, P. Metzner, and J . -L. Burgot, J. Masson, J. , p. 4775. r. shift reagents. -The synthetic routes to and the properties of cyclopropenes, based on the 1974 literature, have been reviewed,'68 and the addition of alkoxycarbenoids to alkynesS6 has already been discussed (p.