A simple conversion of 1-chloroethyl carbonates to fluoroformates: Value in the preparation of tertiary alkyl fluoroformates

DV Anh, RA Olofson, PR Wolf, MD Piteau…

Index: Dang, Vu Anh; Olofson, R. A.; Wolf, Patrick R.; Piteau, Marc D.; Senet, Jean-Pierre G. Journal of Organic Chemistry, 1990 , vol. 55, # 6 p. 1847 - 1851

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Citation Number: 25

Abstract

When the economical and easily available 1-chloroalkyl carbonates (RCHC10C02R') are heated neat or in solution with KF in the presence of an 18-crown-6 catalyst, they fragment to aldehydes (RCHO) and fluoroformates (FC0, R'). If the system is evacuated during reaction and either or both products are removed as formed, then the process is driven to completion and fluoroformates are isolated in good yield. The new methodology (which exemplifies ...