UNUSUAL PHOTOREARRANGEMENTS OF 9,10-DISUBSTITUTED TRIPTYCENE-1,4-QUINONE DERIVATIVES

Authors
BORECKA B GAMLIN JN GUDMUNDSDOTTIR AD OLOVSSON G SCHEFFER JR TROTTER J
Citation
B. Borecka et al., UNUSUAL PHOTOREARRANGEMENTS OF 9,10-DISUBSTITUTED TRIPTYCENE-1,4-QUINONE DERIVATIVES, Tetrahedron letters, 37(13), 1996, pp. 2121-2124
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
13
Year of publication
1996
Pages
2121 - 2124
Database
ISI
SICI code
0040-4039(1996)37:13<2121:UPO9T>2.0.ZU;2-J
Abstract
In contrast to triptycene-1,4-quinone (1a), which forms exclusively a di-pi-methane type product when irradiated in acetonitrile, photolysis of the 9,10-dialkyl-substituted triptycene quinones 1b and 1c leads t o carbene-derived as well as hydrogen atom abstraction-derived photopr oducts. Mechanistic schemes that are capable of rationalizing the resu lts on stereoelectronic grounds are presented and discussed.