Add time:08/17/2019         Source:sciencedirect.com

A regio- and stereoselective cycloaddition of 6,6-spiroepoxycyclohexa-2,4-dienones with indene leading to benzo-annulated spiroepoxytricyclo[5.2.2.02,6]undec-10-en-9-ones has been described. Manipulation of the oxirane ring in adducts furnished benzotricyclo[5.2.2.02,6]undecanes endowed with a β,γ-enone chromophore. Photochemical reaction of β,γ-enones upon direct irradiation (1S) gave annulated bicyclo[4.2.0]octenones as a consequence of a stereoselective 1,3-acyl shift. Triplet excitation of chromophoric systems led to oxa-di-π-methane reaction and gave pentacyclic products which upon cleavage of cyclopropane ring furnished benzoannulated triquinanes. An interesting effect of substituent on the photoreaction has also been observed.

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