Tetrahedron

Reactions of allyloxy (methoxy) carbene in solution. Carbene rearrangement and Claisen rearrangement of the carbene dimer

D Plazuk, J Warkentin, NH Werstiuk

Index: Plazuk, Damian; Warkentin, John; Werstiuk, Nick Henry Tetrahedron, 2005 , vol. 61, # 24 p. 5788 - 5796

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Citation Number: 9

Abstract

Allyloxy (methoxy) carbene, with and without deuterium in the α-position of the allyloxy group, was generated in benzene at 50 and at 110° C. At the higher temperature, the carbene fragmented to allyl and methoxycarbonyl radicals that subsequently coupled. At the lower temperature, most of the carbene dimerised. The structure of the major product and the distribution of deuterium indicated that the dimer underwent Claisen rearrangement at ...