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New skeletal rearrangements via a constrained cyclopropyldicarbinyl diradical generated in the photodecarbonylation of 2,4-diphenyltetracyclo[3.3.2.02, 4.03,7]deca-9-ene-6,8-dione

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
29
Issue
46
Identifiers
DOI: 10.1016/s0040-4039(00)82230-3

Abstract

Abstract Photodecarbonylation of the title diketone ( 1 ) gave 3,3a-diphenyl-3a,7a-dihydroindenone ( 2 ), 1,4-diphenylcyclooctatetraene ( 3 ), and 1,6-diphenylcycloheptatrien-7-ylketene ( 4 ). The reaction pathways are discussed on proposing intermediates of 1.2-diphenyltetracyclo-[4.3.0.0 2,9.0 5,8]non-3-en-7-one ( 11 ) and 1,3-diphenyltricyclo[5.2.0.0 2,9]nona-3,5-dien-8-one( 13 ). Ring expansion of 1 to a 6-membered oxacarbene ( 17 ) was also observed.

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