… Alkylidene Carbenoids with Lithium. ALPHA.-Sulfonyl Carbanions: A Novel Synthesis of Tri-and Tetra-substituted Allenes from 1-Chlorovinyl p-Tolyl Sulfoxides and …

…, T Sakamoto, M Watanabe, K Takano

Index: Satoh, Tsuyoshi; Sakamoto, Tatsuya; Watanabe, Masanori; Takano, Koji Chemical and Pharmaceutical Bulletin, 2003 , vol. 51, # 8 p. 966 - 970

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Citation Number: 31

Abstract

Treatment of 1-chlorovinyl p-tolyl sulfoxides, which were synthesized from ketones and chloromethyl p-tolyl sulfoxide, with ethylmagnesium chloride or isopropylmagnesium chloride at below− 78° C gave magnesium alkylidene carbenoids in about 90% yields. The reaction of the generated carbenoids with lithium α-sulfonyl carbanions was found to afford tri-and tetra-substituted allenes. Both cyclic ketones and acyclic ketones were useful in ...