Extended pi-participation in biomimetic cyclization of squalene derivatives

被引：0

作者：

Borcic, S ^{[1
]}

Humski, K ^{[1
]}

Kronja, O ^{[1
]}

Malnar, I ^{[1
]}

机构：

[1] UNIV ZAGREB,DEPT CHEM,FAC PHARM & BIOCHEM,ZAGREB 10000,CROATIA

来源：

CROATICA CHEMICA ACTA | 1996年 / 69卷 / 04期

关键词：

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chlorides 4(1-aryl-1-chloro-5,9,14,18,22-pentamethyl-5,9,13,17,21-tricosapentaenes) with various phenyl substituents were prepared, and solvolysis rates were measured in aqueous ethanol (phi = 95% and 80%) and in aqueous 2,2,2-trifluoroethanol (omega = 97%). Hammett rho(+) values obtained are -1.86, -1.81 and -1.56, respectively, suggesting concerted cyclization of at least two double bonds in the rate determining step.

引用

页码：1347 / 1359

页数：13

共 50 条

[41] THE PREPARATION OF NEW BIS(1,3-DITHIOLE) DERIVATIVES - EXTENDED PI-DONORS FOR ORGANIC METALS
BRYCE, MR
MOORE, AJ
TETRAHEDRON LETTERS, 1988, 29 (09) : 1075 - 1078
[42] STEREOSPECIFIC CYCLIZATION OF CIS,CIS-1,5-CYCLONONADIENE TO CIS-HEXAHYDROINDANE DERIVATIVES VIA C+-PI INTERACTION
NAGENDRAPPA, G
DEVAPRAB.D
TETRAHEDRON LETTERS, 1970, (54) : 4687 - +
[43] EXTENSION OF THE AZA-DI-PI-METHANE REACTION TO STABLE DERIVATIVES - PHOTOCHEMICAL CYCLIZATION OF BETA,GAMMA-UNSATURATED OXIME ACETATES
ARMESTO, D
HORSPOOL, WM
LANGA, F
RAMOS, A
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (01): : 223 - 228
[44] Nucleophilic participation in the solvolyses of (Arylthio)methyl chlorides and derivatives: Application of simple and extended forms of the Grunwald-Winstein equations
D'Souza, M. J. (dsouzama@wesley.edu), 1600, Bentham Science Publishers (16):
[45] Nucleophilic Participation in the Solvolyses of (Arylthio)methyl Chlorides and Derivatives: Application of Simple and Extended Forms of the Grunwald-Winstein Equations
Kevill, Dennis N.
Park, Young Hoon
Park, Byoung-Chun
D'Souza, Malcolm J.
CURRENT ORGANIC CHEMISTRY, 2012, 16 (12) : 1502 - 1511
[46] Lack of a secondary β-deuterium kinetic isotope effect in the solvolysis of 2-chloro-3-hydrosqualene. A case of extended π-participation and indication of concerted biomimetic polycyclization
1600, (113):
[47] STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .14. SOLVOLYSIS OF 2-ARYL-2-BENZONORBORNENYL PARA-NITROBENZOATES - APPLICATION OF TOOL OF INCREASING ELECTRON DEMAND AS A TEST FOR PI-PARTICIPATION IN HIGH EXO-ENDO RATE RATIOS
BROWN, HC
IKEGAMI, S
LIU, KT
TRITLE, GL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (09) : 2531 - 2536
[48] TERPENES AND TERPENE DERIVATIVES .16. BIOMIMETIC CYCLIZATION OF 2-(3-BUTENYL)-3,4-DIMETHYL-2-CYCLOHEXEN-1-OL
GOTTSCHALK, FJ
MARSCHALLWEYERSTAHL, H
WEYERSTAHL, P
LIEBIGS ANNALEN DER CHEMIE, 1985, (03): : 462 - 467
[49] STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .13. EFFECT OF INCREASING ELECTRON DEMAND ON RATES OF SOLVOLYSIS OF 1-ARYLCYCLOPENT-3-EN-L-YL AND 1-ARYLCYCLOPENTYL PARA-NITROBENZOATES - EVIDENCE FOR ABSENCE OF PI-PARTICIPATION
PETERS, EN
BROWN, HC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (26) : 7454 - 7457
[50] PI PARTICIPATION AND EXO - ENDO RATE RATIOS IN SOLVOLYSIS OF METHOXY- AND NITRO-SUBSTITUTED BENZONORBORNEN-2-YL DERIVATIVES
BROWN, HC
TRITLE, GL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (10) : 2689 - &

← 1 2 3 4 5 →