Journal of Organic Chemistry p. 3007 - 3011 (1988)
Update date:2022-09-26
Topics:
Murray, Robert W.
Pillay, M. Krishna
Jeyaraman, Ramasubba
Treatment of quadricyclane (2) with dimethyldioxirane (1) leads to the formation of exo-norborna-2,5-diene monoepoxide (4), exo,exo-norborna-2,5-diene diepoxide (5), bicyclo<3.1.0>hex-2-ene-6-endo-carboxaldehyde (6), and exo-2,3-epoxybicyclo<3.1.0>hexane-6-endo-carboxaldehyde(7).The reaction is believed to involve prior catalyzed isomerization of 2 by 1 to norbornadiene (3) and subsequent conversion of 3 to the observed products.Under suitable conditions 1 reacts with 3 to give 4 and 6 in a 97:3 distribution, respectively.
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