Tetrahedron

Reformatsky-type reaction of α-haloketones promoted by titanium tetraiodide

M Shimizu, F Kobayashi, R Hayakawa

Index: Shimizu, Makoto; Kobayashi, Fumiko; Hayakawa, Ryuuichirou Tetrahedron, 2001 , vol. 57, # 47 p. 9591 - 9595

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Citation Number: 32

Abstract

We have recently found that TiI 4 is an excellent reagent for the reduction of α-diketones and/or sulfoxides, and that it also induces ring-opening-aldol reaction of methoxyallene oxide and pinacol coupling of aldehyhdes. 5 In these reactions, Ti(IV) was thought to be responsible for such facile reductions. In particular, the ability of the iodide ion to displace the iodine α to the carbonyl appears to be responsible for the facile aldol type reaction of methoxyallene ...