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Synlett 2001; 2001(Special Issue): 1046-1049
DOI: 10.1055/s-2001-14658
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Synthesis of Cyclopentenediolates and Cyclopentane-1,2-diones by Carbonylation of Titanacyclobutane Complexes Prepared by Free Radical Alkylation

Charles A. G. Carter* , Gary L. Casty, Jeffrey M. Stryker
  • *Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2 Canada; Fax + 1 (780) 4 92 82 31; E-mail: jeff.stryker@ualberta.ca
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Publication Date:
31 December 2001 (online)

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The synthesis of titanium cyclopentenediolates by the double carbonylation of titanacyclobutane complexes is reported, a process known as the Bercaw carbonylation. The reaction is general for a range of titanacyclobutanes prepared by free radical alkylation of allyltitanium(III) precursors. Titanacyclobutane formation and carbonylation can be conducted in one pot without the isolation of sensitive intermediates. Subsequent conversion to lithium cyclopentenediolates and cyclopentane-1,2-diones provides access to a range of synthetically valuable organic products.

carbonylations - titanium - enediolates - metallacyclobutane complexes - cyclopentane-1,2-diones