Metal-assisted reactions. Part 27.1 3-Benzyloxy-1,2-benzisothiazole 1,1-dioxide: an unusual ether linkage that does not permit heterogeneous catalytic hydrogenolysis

Abstract

Aryl or allyl ethers of some heterocyclic systems can be readily hydrogenolysed or cross-coupled catalytically with transition metals to give arenes, alkenes or alkanes. Unexpectedly for transition metals, the corresponding alkyl and, particularly, benzyl ethers are totally inert. An X-ray structure determination on 3-benzyloxy-1,2-benzisothiazole 1,1-dioxide 1 has shown that there is no inherent structural reason for this major difference, apart from the absence of a suitable p-orbital in the benzyl ethers.