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[,7]oct-3-en-8-one and Its Related Compounds
Makoto NittaAkihiko OmataShuji Okada
Author information

1984 Volume 57 Issue 6 Pages 1505-1509


The cycloaddition reactions of 1,5-dimethyl-6-methylenetricyclo[,7]oct-3-en-8-one (1a), its corresponding -8-endo-ol (1b), 1,5,8-trimethyltricyclo[,7]oct-3-en-8-endo-ol (1c), and 5,8-dimethyl-9-methylenetricyclo[,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[,7]oct-3-en-8-one with MNO or PA was also studied to prove the regioselectivity of the cycloadditions of constrained vinylcyclopropane moiety.

Information related to the author

This article cannot obtain the latest cited-by information.

© The Chemical Society of Japan
Previous article Next article