ELECTRON-TRANSFER-INDUCED STEREOSELECTIVE CYCLIZATION OF 2,2-DISUBSTITUTED DIBENZOYLMETHANE TO ANTI-1,2-CYCLOPROPANEDIOL

Authors
HASEGAWA E KATAGI H NAKAGAWA D HORAGUCHI T
Citation
E. Hasegawa et al., ELECTRON-TRANSFER-INDUCED STEREOSELECTIVE CYCLIZATION OF 2,2-DISUBSTITUTED DIBENZOYLMETHANE TO ANTI-1,2-CYCLOPROPANEDIOL, Tetrahedron letters, 36(38), 1995, pp. 6915-6918
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
38
Year of publication
1995
Pages
6915 - 6918
Database
ISI
SICI code
0040-4039(1995)36:38<6915:ESCO2>2.0.ZU;2-9
Abstract
Irradiation of 2,2-dimethyl-13-diphenyl-13-propanedione in the presenc e of triethylamine gave anti-2,2-dimethyl-13-diphenyl-13-cyclopropaned iol as a major product. On the basis of the results obtained, the mech anism involving single electron transfer between the excited diketone and the ground state amine followed by the anion radical rearrangement was proposed. The same cyclized product was also obtained for the rea ction with samarium diiodide.