Tetrahedron

Silylation as a protective method for terminal alkynes in oxidative couplings: A general synthesis of the parent polyynes H (C C) nH (n= 4–10, 12)

R Eastmond, TR Johnson, DRM Walton

Index: Eastmond,R. et al. Tetrahedron, 1972 , vol. 28, p. 4601 - 4616

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Citation Number: 356

Abstract

Individual polyynes in the series H (C C) n (n= 4–10, 12) have been prepared in solution by sequences involving Cu-catalysed oxidative couplings (Hay technique) of silyl-protected terminal alkynes, partial cleavage (desilylation) of the products by alkali, recoupling and complete desilylation. Thus using the conditions established in a model coupling, Et3SiC CH (I)→ Et3Si (C SiEt3 (II), coupling of the silyidiyne Et3Si (C C) 2H (II) gives Et3Si (C ...