Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
1,3-Dipolar Cycloaddition Reactions of 6-Methylenetricyclo[3.2.1.02,7]oct-3-en-8-one and Its Related Compounds
Makoto NittaAkihiko OmataShuji Okada
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1984 Volume 57 Issue 6 Pages 1505-1509

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Abstract

The cycloaddition reactions of 1,5-dimethyl-6-methylenetricyclo[3.2.1.02,7]oct-3-en-8-one (1a), its corresponding -8-endo-ol (1b), 1,5,8-trimethyltricyclo[3.2.1.02,7]oct-3-en-8-endo-ol (1c), and 5,8-dimethyl-9-methylenetricyclo[3.3.1.02,8]non-3-en-7-one (2) were investigated in order to study the origin of its stereoselectivity or site selectivity. The reaction of 2,4,6-trimethylbenzonitrile oxide (mesitonitrile oxide, MNO) with 1a, b occurs on the exo-mthylene group from the exo-side, but on the endocyclic double bond in the case of 1c. The compound 2 undergoes the addition of MNO on both the exocyclic and endocyclic double bonds to give a corresponding bis-adduct. On the other hand, the reaction of phenyl azide (PA) with 1ac occurs on the endocyclic double bond from the endo-side to give a single adduct. The reaction of 6-exo-methoxy-1,5,6-trimethyltricyclo[3.2.1.02,7]oct-3-en-8-one with MNO or PA was also studied to prove the regioselectivity of the cycloadditions of constrained vinylcyclopropane moiety.

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