European Journal of Organic Chemistry

On the Origin of E/Z Selectivity in the Modified Julia Olefination–Importance of the Elimination Step

R Robiette, J Pospíšil

文献索引：Robiette, Raphael; Pospisil, Jiri European Journal of Organic Chemistry, 2013 , # 5 p. 836 - 840

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被引用次数: 4

摘要

Abstract The mechanism and origin of high E selectivity in the modified Julia olefination of aromatic aldehydes have been explored by computational and experimental means. Reversibility of addition and hence selectivity of the formation of sulfinate 5 is very variable and depends on the nature of the sulfone substrate. However, in all cases, elimination occurs through a concerted antiperiplanar and synperiplanar mechanism for sulfinates ...