Conformational effects on the 2, 3-sigmatropic shift of sulfur-stabilized ylides and enolates involving bicyclic transition states

E Vedejs, MJ Arnost, JP Hagen

Index: Vedejs,E. et al. Journal of Organic Chemistry, 1979 , vol. 44, p. 3230 - 3238

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Citation Number: 69

Abstract

21 28 therefore less than 1 h at-22" C. However, similar treatment of 2 with LDA and CHJ gave exclusively the unrearranged C-methylated product 24. Even after the anion 23 was heated to 50" C in THF, methylation gave 24 (low material balance) and none of the sulfide derived from rearranged anion 25. Similar experiments with the six-membered ring system 1 at 0" C or below again gave only unrearranged products. Under more forcing conditions (> ...