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Synlett 1997; 1997(10): 1181-1183
DOI: 10.1055/s-1997-992
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Intramolecular C-H Insertion Reactions of Acetoxy Fischer Carbene Complexes

Kei Takeda* , Yasushi Okamoto, Akemi Nakajima, Eiichi Yoshii, Toru Koizumi
  • *Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-01, Japan, Internet takedak@ms.toyama-mpu.ac.jp
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Publication Date:
31 December 2000 (online)

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The reaction of 4-substituted 2-(t-butyldimethylsiloxy)-1,3-butadiene with acetoxy chromium Fischer carbene complexes afforded bicyclo[4.1.0]heptene derivative 3, 18, an intramolecular C-H insertion product of the initially formed Diels-Alder adduct 6. The role of the metal and the heteroatom ligand in the carbene complex, and of the substituent at 3-position in 6 on the C-H insertion has been examined.

C-H insertion - Fischer carbene complex - bicyclo[4.1.0]heptene - Diels-Alder reaction