7-ALKYL-7-HYDROXYMETHYL-3,4-DIMETHOXYNORCARADIENES - A NEW-TYPE OF NORCARADIENE STABILIZED BY PI-DONORS

Authors
MATSUMOTO M SHIONO T KASUGA NC
Citation
M. Matsumoto et al., 7-ALKYL-7-HYDROXYMETHYL-3,4-DIMETHOXYNORCARADIENES - A NEW-TYPE OF NORCARADIENE STABILIZED BY PI-DONORS, Tetrahedron letters, 36(48), 1995, pp. 8817-8820
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
48
Year of publication
1995
Pages
8817 - 8820
Database
ISI
SICI code
0040-4039(1995)36:48<8817:7-ANON>2.0.ZU;2-C
Abstract
Introduction of an alkyl (aralkyl) substituent at the 7-position of 7- ethoxycarbonyl-3,4-dimethoxynorcaradiene (7a) gives fairly stable norc aradienes (NCD) (7b-f). The reduction products (8b-f) of NCD (7b-f) ex ist mainly as NCD form especially at low temperature, although 8b-f po ssess no longer any pi-acceptor at the 7-position. The present results clarify that two methoxyl groups as the pi-donors at the 3,4-position stabilize the NCD structure.