Facile and efficient syntheses of carboxylic anhydrides and amides using (trimethylsilyl) ethoxyacetylene

…, S Akai, N Ajimura, M Yoshigi, T Tsugoshi…

Index: Kita, Yasuyuki; Akai, Shuji; Ajimura, Naomi; Yoshigi, Mayumi; Tsugoshi, Teruhisa; et al. Journal of Organic Chemistry, 1986 , vol. 51, # 22 p. 4150 - 4158

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Citation Number: 102

Abstract

(Trimethylsilyl) ethoxyacetylene, a stable and easy-handling reagent, serves as an excellent dehydrating agent for the synthesis of carboxylic anhydrides and amides from the corresponding carboxylic acids. By means of this reagent, various types of acid-sensitive carboxylic anhydrides and amides were obtained almost in quantitative yields. Twenty-two examples of carboxylic anhydrides and 12 examples of amides were presented.

~97%

~80%

~99%

~94%

~94%

~94%

~98%

~96%

~52%

~97%

~79%

~99%

~94%

Intramolecular cycloaddition reactions of furo [3, 4-b] indo...

[Bahadur, Gulam A.; Baylei, A. Sydney; Middleton, Nigel W.; Peach, Josephine M. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 1688 - 1692]

A mild and facile synthesis of carboxylic anhydrides

[Kita, Y.; Akai, S.; Yoshigi, M.; Nakajima, Y.; Yasuda, H.; Tamura, Y. Tetrahedron Letters, 1984 , vol. 25, # 52 p. 6027 - 6030]