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Paper | Regular issue | Vol 31, No. 1, 1990, pp.115-122
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5154
On the Multiplicity of Carbenes Conjugated with Pyrrole and Furan Moieties: Molecular Orbital Calculation and Reaction of 2-(1-Methyl)pyrrolylmethylene and 2-Furylmethylene with cis- and trans-Stilbenes

Katsuhiro Saito,* Takahiro Ushida, Hiroshi Fushihara,Yoshiro Yamashita, Shoji Tanaka, and Kensuke Takahashi

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan


The reaction of 2-(1-methyl)pyrrolylmethylene and 2-furylmethylene with cis- and trans-stilbenes proceeded in a stereospecific manner to give the corresponding cyclopropane derivatives to show that the multiplicities of these carbenes are singlet. The molecular orbital calculation showed that these carbenes are triplet in their ground state and nucleophilic both in singlet and triplet states.