By H Suschitzky; O Meth-Cohn; Great Britain. The Royal Society of Chemistry

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The iodide- (or bromide-)catalysed rearrangements of (260; R = H, alkyl, or aryl) to (261) 194 '91 196 '91 198 199 E. R. Talaty, K. C. Bengtsson, and L. M. Pankow, Synth. , 1980,10,99. K. Maruyama, H. Tsukube, and T. Araki, J. Chem. , Chem. , 1980,1222. B. Merah and F. Texier, Bull. Chim. , Part2, 1980, 552. H. Stamm, A . Woderer, and W. Wiesert, Chem. , 1981, 114, 3 2 . E. R. Talaty, A . R. Clague, M. 0. Agho, M. N. Deshpande, P. M. Courtney, D. H. Burger. and E. F. Roberts, J. Chem. ,Chem.

Kilaas, Tetrahedron, 1979,35, 2583. N. N. Magdesieva and N. G. Chovnikova, Zh. Org. , 1979, 15, 2402 (Chem. , 1980, 93,46 268). W. C. Still and V. J. Novack, J. Am. Chem. ,1981,103,1283. T. Katsuki and K. B. Sharpless, J. A m . Chem. , 1980,102, 5974. Three-Membered Ring Systems 11 added Bu‘OOH and the ally1 alcohol substrate. Normally, after a period in the freezer overnight, the product may be isolated in good yield. The method possesses two striking features. ) of configuration 2S,3S. (ii) Upon use of a given tartrate enantiomer, the system seems obliged to deliver the epoxide oxygen from the same enantioface of the alkene, regardless of the substitution pattern.

A m . Chem. ,1980,102,2095. L. Thijs and B. Zwanenburg, Tetrahedron, 1980, 36, 2145. G. D. Annis, S. V. Steven, C. R. Self. and R. Sivararnakrishnan,J. Chern. ,Perkin Trans. 1, 1981,270. 169This difference has been accounted for in terms of strain in the oxiran ring. Elimination in the relatively unstrained compound (213; R = SO,Et, n = 3) proceeds at only 20 times the rate of that of (215). 14 was obtained for the conversion of (213; R = variously substituted phenyl, n = 1) into the corresponding ally1 alcohols (214) when using Bu'OK in Bu'OH, indicating that a carbanion develops at the benzilic carbon during the r e a ~ t i 0 n .

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