Electron transfer induced deprotonation of alpha- and beta-pinene: Evidence for ring-closed vinylcyclobutane radical cations

被引：14

作者：

Zhou, DH ^{[1
]}

Sheik, M ^{[1
]}

Roth, HD ^{[1
]}

机构：

[1] RUTGERS STATE UNIV,WRIGHT RIEMAN LABS,NEW BRUNSWICK,NJ 08855

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 14期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/0040-4039(96)00332-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Electron transfer from alpha- (1) or beta-pinene (2), to 2,3,5,6-tetrachlorobenzoquinone generates radical cations, which are rapidly deprotonated by the semiquinone radical anion. (1S,5S)-2 is converted to (1S,5S)-1 and (1R,5R)-1 yields a dehydrogenation product, verbenene, (1R,5R)-9 with essentially quantitative retention of optical: activity. The results support chiral, ''ring-closed'' radical cation structures in which the allylic-quaternary cyclobutane C-C bond retains a significant degree of bonding. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：2385 / 2388

页数：4

共 29 条

[1]

PHOTOCHEMICAL AND ESR SPECTRAL EVIDENCE FOR A STEREOSELECTIVE REARRANGEMENT OF RADICAL CATIONS DERIVED FROM AZOALKANES AND BICYCLOPENTANES [J].

ADAM, W ;

WALTER, H ;

CHEN, GF ;

WILLIAMS, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3007-3014

[2]

THE PHOTOCHEMICAL NUCLEOPHILE OLEFIN COMBINATION, AROMATIC-SUBSTITUTION (PHOTO-NOCAS) REACTION .5. METHANOL-MONOTERPENES (ALPHA-PINENE AND BETA-PINENE, TRICYCLENE, AND NOPOL), 1,4-DICYANOBENZENE [J].

ARNOLD, DR ;

DU, XY .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (02) :403-414

[3]

THE PHOTOCHEMICAL NUCLEOPHILE OLEFIN COMBINATION, AROMATIC-SUBSTITUTION REACTION - METHANOL-ALPHA-PINENE-1,4-DICYANOBENZENE AND BETA-PINENE-1,4-DICYANOBENZENE - THE PHOTO-NOCAS REACTION [J].

ARNOLD, DR ;

DU, XY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7666-7667

[4]

BAULD N, 1987, ACCOUNTS CHEM RES, V20, P180

[5]

THE THEORETICAL REACTION-PATH FOR THE CATION RADICAL VINYLCYCLOBUTANE REARRANGEMENT - A CONCERTED SR PATH [J].

BAULD, NL .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (07) :896-898

[6]

COORDINATION OF SILVER ION WITH UNSATURATED COMPOUNDS .9. SOLID COMPLEXES OF SILVER SALTS WITH CYCLOHEXENE, ALPHA-PINENE AND BETA-PINENE [J].

COMYNS, AE ;

LUCAS, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (16) :4339-4341

[7]

ACCELERATING SYMMETRY FORBIDDEN REACTIONS - THE VINYLCYCLOPROPANE-]CYCLOPENTENE CATION RADICAL REARRANGEMENT [J].

DINNOCENZO, JP ;

CONLON, DA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2324-2326

[8]

CYCLOPROPANE STEREOMUTATION CATALYZED BY ONE-ELECTRON OXIDANTS [J].

DINNOCENZO, JP ;

SCHMITTEL, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (05) :1561-1562

[9]

ABINITIO CALCULATIONS ON THE RING-OPENING OF CYCLOPROPANE RADICAL CATION - TRIMETHYLENE RADICAL CATION IS NOT A STABLE INTERMEDIATE [J].

DU, P ;

HROVAT, DA ;

BORDEN, WT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3405-3412

[10]

Physical properties of terpenes. I. The system alpha- and beta-pinene [J].

Fuguitt, RE ;

Stallcup, WD ;

Hawkins, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :2978-2981

← 1 2 3 →