Titanocene(II)-Promoted Cyclization of Unsaturated Thioacetals

Tooru Fujiwara; Takeshi Takeda

doi:10.1055/s-1999-2618

Synlett 1999; 1999(3): 354-356
DOI: 10.1055/s-1999-2618

letter

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Titanocene(II)-Promoted Cyclization of Unsaturated Thioacetals

Tooru Fujiwara^* , Takeshi Takeda

^*Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan; Fax 81 42 3 88 70 34; E-mail: takeda-t@cc.tuat.ac.jp

Abstract

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The low-valent titanium species-promoted transformation of unsaturated thioacetals to cyclic compounds was studied. The cyclization of thioacetals having an olefin moiety proceeded with the loss of terminal olefin carbon to produce the corresponding five-, six-, and seven-membered cycloalkenes when they were treated with the low-valent titanium species Cp₂Ti[P(OEt)₃]₂ in refluxing THF. The similar reactions of 1-[3,3-bis(phenylthio)propoxy]-2-(prop-1- and prop-2-enyl)benzenes gave the seven- and eight-membered unsaturated cyclic ethers, respectively.

titanocene(II) - thioacetal - cyclization - ring-closing metathesis

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