General reactivity of 2-lithiobenzothiazole to various electrophiles and the use as a formyl anion equivalent in the synthesis of. ALPHA.-hydroxy carbonyl compounds.

H Chikashita, M Ishibaba, K Ori, K Itoh

文献索引：Chikashita, Hidenori; Ishibaba, Megumi; Ori, Keiji; Itoh, Kazuyoshi Bulletin of the Chemical Society of Japan, 1988 , vol. 61, p. 3637 - 3648

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被引用次数: 51

摘要

The reaction of 2-lithiobenzothiazole with a variety of electrophiles such as aldehydes, ketones, carboxylic esters, lactones, nitriles, and amides afforded the expected addition and substitution products. Trimethylsilyl chloride readily reacted with the benzothiazolyl anion to give 2-trimethylsilylbenzothiazole, while common alkyl halides including primary iodide and benzyl halides, as well as epoxides, did not react with the anion. This characteristic ...