TITANIUM-MEDIATED REACTION OF CYCLOHEPTATRIENE WITH ALDEHYDES - A NEWELECTRON-REVERSED APPROACH TO THE FUNCTIONALIZATION OF 7-MEMBERED RING

Authors
SZYMONIAK J FELIX D MOISE C
Citation
J. Szymoniak et al., TITANIUM-MEDIATED REACTION OF CYCLOHEPTATRIENE WITH ALDEHYDES - A NEWELECTRON-REVERSED APPROACH TO THE FUNCTIONALIZATION OF 7-MEMBERED RING, Tetrahedron letters, 35(46), 1994, pp. 8613-8616
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
46
Year of publication
1994
Pages
8613 - 8616
Database
ISI
SICI code
0040-4039(1994)35:46<8613:TROCWA>2.0.ZU;2-9
Abstract
The cycloheptenyl-eta(3)-allyltitanium species prepared starting from cycloheptatriene by the action of titanocene dichloride and an alkyl G rignard reagent, undergo in situ addition to aldehydes to produce a mi xture of isomeric 1,4- and 1,3-cycloheptadienyl alkyl (aryl) carbinols , 3 and 2 respectively. The increasing 3/2 ratio with the increase of steric hindrance in aldehyde was observed. The reaction opens a simple way to the variously functionalized 1,4-cycloheptadienes, some of whi ch are closely related to biologically active compounds.