By M A McKervey, Chemical Society
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Additional info for Alicyclic chemistry. Vol. 6 : a review of the literature published during 1976
A. Doutheau and J. Gore, Bull. chim. France, 1976, 1189. (a) M. Sato, J. Tsunetsugu,and S. Ebine, Bull. Chem. Japan, 1976,49,2230; (b)B. Muller and P. Weyerstahl, Tetrahedron, 1976, 32, 865. Three-membered Rings 19 Steric factors are often of significance in the addition reactions of carbenes. Attempts to prepare the tetracycle (57) by dihalogenocarbene addition to ( 5 5 ; R = H) fail since bis-addition cannot be prevented. 75 Br (59) (58) R=H 13% R = OBu' 30% (40; R = H) @ + 3rd 3r Br 60 40 Organometallic, Thermal, and Photochemical Methods.
1976. 15. 240. 104The yields of cyclopropane products match those of the Simmons-Smith method when dihalogenomethanes are used, and with trihalogenomethanes monohalogenocyclopropanes are produced in a reaction which demonstrates a syn selectivity. 1 :1. The reaction with act-dibromoacetic esters also shows a syn selectivity when steric interaction between the alkoxycarbonyl group and the substituents of the olefin is not significant; with terminal olefins the cis-isomer of the product cyclopropane predominates.
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. 15). ' Dehydrobromination of the analogous 1-bromocyclopropyl esters is unsuccessful.
Alicyclic chemistry. Vol. 6 : a review of the literature published during 1976 by M A McKervey, Chemical Society