Tetrahedron

Reactivity of triethyl phosphite with tetrachloromethane: electron transfer versus ionic substitution on “positive” halogen

S Bakkas, M Julliard, M Chanon

Index: Bakkas, Salem; Julliard, Michel; Chanon, Michel Tetrahedron, 1987 , vol. 43, # 3 p. 501 - 512

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Citation Number: 13

Abstract

The reaction [1] of triethyl phosphite (1) with tetrachloromethane (2) has been studied from a mechanistic point of view. 1 reacts at 80° C with 2 to form diethyltrichloromethanephosphonate (03)(85–90% yield) and chloroethane (4)(80% yield). Several resulta hint at a radical chain mechanism (like SRN1). Trichloromethyl radical is trapped by 2, 6-di-t-butyl-4-cresol (BHT), the reaction may be initiated with UV radiation ( ...