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Synlett 1999; 1999(3): 354-356
DOI: 10.1055/s-1999-2618
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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
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Publication Date:
31 December 1999 (online)

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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