Stereoelectronic and homoconjugative effect of stereoselectivity. The addition of dichlorocarbene to 1,5-dimethyl-6-methylenetricyclo(3.2.1.02,7)oct-3-en-8-one and its related compounds.

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概要

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• The reaction of dichlorocarbene with 1,5-dimethyl-6-methylenetricyclo[3.2.1.0<SUP>2,7</SUP>]oct-3-en-8-one, its corresponding alcohol derivative, and 1,5,8-trimethyl-6-methylenetricyclo[3.2.1.0<SUP>2,7</SUP>]oct-3-en-8-<I>endo</I>-ol occurs on the exocyclic double bond to give <I>exo</I> and <I>endo</I> adducts with preferential formation of the <I>exo</I> adduct. Dichlorocarbene addition to 1,3,5-trimethyl-6-methylenetricyclo[3.2.1.0<SUP>2,7</SUP>]oct-3-en-8-one (<B>1d</B>) occurs on the endocyclic double bond from the <I>exo</I> side, while the reaction occurs on the exocyclic double bond from both the <I>exo</I> and <I>endo</I> sides in the case of the corresponding alcohol derivative. The stereoselectivity or site selectivity was discussed on the basis of the stereoelectronic and homoconjugative effects as well as the steric effect of the reaction. Several chemical transformations, along with the derivation of bis adducts of dichlorocarbene, were also studied for confirmation of the structure of mono adducts. 1,3-Dipolar cycloaddition of <B>1d</B> and its dichlorocarbene adduct with mesitonitrile oxide, giving the adducts on the exocyclic double bond, was also studied to suggest a possible causative factor to control the electrophilic addition in the indicated direction.

• 公益社団法人 日本化学会の論文

著者

• Nitta Makoto

  Department Of Applied Pharmacology Toyama Medical And Pharmaceutical University

• Kato Masami

  Department Of Clinical Laboratory Science Kanazawa University Graduate School Kanazawa University

• Okada Shuji

  Department of Chemistry, School of Science and Engineering, Waseda University

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