The Journal of Organic Chemistry

Stepwise cycloadditions of pentadienyllithiums to 1, 3-dienes

M Newcomb, WT Ford

Index: Newcomb,M.; Ford,W.T. Journal of Organic Chemistry, 1974 , vol. 39, p. 232 - 236

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Citation Number: 4

Abstract

Results An initially equimolar THF solution of furan and pentadienyllithium (l), generated from 1, 4-pentadiene and n-butyllithium, after 18 hr at 25" contained no 1 by pmr. Addition of excess D20 to the solution followed by distillation produced furan-2-d in 37% yield, and two fractions less volatile than THF in 24 and 10% yields based on 1, 4-pentadiene. Glpc analysis showed that the two fractions contained at least four and ten components, ...