ACID-CATALYZED REARRANGEMENT OF PHENYLSUBSTITUTED 1,3-BISHOMOCUBANONEVIA SEVERAL EQUILIBRATING NONCLASSICAL BICYCLOBUTONIUM IONS

Authors
OGINO T OHTAKI N YAMAI S WADA F AWANO K
Citation
T. Ogino et al., ACID-CATALYZED REARRANGEMENT OF PHENYLSUBSTITUTED 1,3-BISHOMOCUBANONEVIA SEVERAL EQUILIBRATING NONCLASSICAL BICYCLOBUTONIUM IONS, Tetrahedron letters, 35(27), 1994, pp. 4793-4796
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
27
Year of publication
1994
Pages
4793 - 4796
Database
ISI
SICI code
0040-4039(1994)35:27<4793:AROP1>2.0.ZU;2-2
Abstract
lpentacyclo[5.3.0.0(2,5).0(3,9).0(4,8)]decan-6-one in acetic acid unde rgoes H2SO4-catalyzed rearrangement to give two isomeric acetoxyketone s having a novel tricyclo[5.2.1.0(4,8)]dec-2-ene ring system besides a small amount of 2,3-dihydro-7-phenyl-1(8H)-azulenone. The formation o f the acetoxyketones can best be accounted by assuming equilibration o f several structurally different non-classical bicyclobutonium ion int ermediates.