Rate Enhancement of the Radical 1,2-Acyloxy Shift (Surzur-Tanner Rearrangement) by Complexation with Lewis Acids

Emmanuel Lacôte; Philippe Renaud

doi:10.1002/(SICI)1521-3773(19980904)37:16<2259::AID-ANIE2259>3.0.CO;2-U

Rate Enhancement of the Radical 1,2-Acyloxy Shift (Surzur-Tanner Rearrangement) by Complexation with Lewis Acids

Angew Chem Int Ed Engl. 1998 Sep 4;37(16):2259-2262. doi: 10.1002/(SICI)1521-3773(19980904)37:16<2259::AID-ANIE2259>3.0.CO;2-U.

Authors

Emmanuel Lacôte¹, Philippe Renaud¹

Affiliation

¹ Institut de chimie organique, Université de Fribourg, Pérolles, CH-1700 Fribourg (Switzerland), Fax: (+41) 263-009-739.

Abstract

New prospects for synthetic applications are offered by the 1,2-acyloxy shift of β-(acyloxy)alkyl radicals, which proceeds with high yields under Lewis acidic conditions [Eq. (1)]. With the exception of cyclizations, this is the first Lewis acid mediated acceleration of a radical rearrangement.

Keywords: Aluminum; Lewis acids; Radical reactions; Rearrangements; Scandium.