Olefin synthesis by reaction of stabilized carbanions with carbene equivalents. 1. Use of (iodomethyl) tributylstannane for methylenation of sulfones

BA Pearlman, SR Putt, JA Fleming

Index: Pearlman, Bruce A.; Putt, Sterling R.; Fleming, Jeffrey A. Journal of Organic Chemistry, 1985 , vol. 50, # 19 p. 3622 - 3624

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Citation Number: 24

Abstract

ORefer to eq 1. All experiments listed in the table were performed by treating a solution of the sulfone in THF (0.20 M for la, 0.12 M for lb) with 1.1 equiv of n-BuLi (-78" C, 5 min) followed by i-PrzNH (0.2-0.6 equiv,-78" C, 10 min), followed by 1.5 equiv of alkylating agent.* The period of time required for the alkylation to reach 50% conversion (at-78" C). eChromatographically and spectroscopically ('H NMR and 13C NMR) homogeneous ...