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Synlett 1995; 1995(6): 625-627
DOI: 10.1055/s-1995-5011
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A Unique Solvent Effect Governing Periselectivity of the Carbene Transfer from Fischer Carbene Complexes: Mechanism, Scope and Limitation of Their Formal [3+2] Cycloaddition to Electron-Deficient Olefins

Matthias Hoffmann, Hans-Ulrich Reissig*
  • *Institut für Organische Chemie der Technischen Universität Dresden, Mommsenstrasse 13, D-01062 Dresden, Germany
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Publication Date:
31 December 2000 (online)

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Thermal reaction of pyrrolyl-substituted carbene complex 3 with several electron-deficient alkenes afforded cyclopentene derivatives such as 6, 8, and 10 in a formal [3+2] cycloaddition in reasonable yields if cyclohexane was employed as solvent. A very surprising solvent effect was uncovered allowing selective synthesis of vinylcyclopropane derivatives 12 or 16 in solvents with good donor quality. A plausible mechanism is suggested which considers the parameters influencing the competition between [3+2] and [2+1] cycloaddition.

Chromium Carbene Complexes - [3+2] Cycloaddition - Cyclopentene Derivatives - Vinylcyclopropanes - Solvent Effect