Regioselectivity of ring closure of the 2-azonia-2,2,5-trimethyl-5-hexenyl radical

被引：8

作者：

Della, EW ^{[1
]}

Smith, PA ^{[1
]}

机构：

[1] Flinders Univ S Australia, Dept Chem, Bedford Pk, SA 5042, Australia

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 03期

基金：

澳大利亚研究理事会;

关键词：

alpha-ammonio radicals; heterocyclic synthesis; regioselectivity; radical cyclisation;

D O I：

10.1016/S0040-4039(00)01987-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 2-azonia-2,2,5-trimethyl-5-hexenyl radical 9, derived from treatment of 1-iodo-2,2,5-trimethyl-2-azonia-5-hexenyl iodide 12 with tributyltin hydride, is found to give an 8:3:1 mixture of the isomeric 5-exo, 6-endo and acyclic ammonium salts. A rationale for the observed regioselectivity is proposed, and a comparison is made with the behaviour of the corresponding all-carbon radical. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：481 / 483

页数：3

共 15 条

[1] CONFORMATIONAL ANALYSIS .9. THE GEM-DIMETHYL EFFECT [J].

ALLINGER, NL ;

ZALKOW, V .

JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (05) :701-704

[2] AZETIDINES .4. REACTION OF 1,1-DIMETHYL- 1-BENZYL-1-METHYL- AND 1,1-DIBENZYL-3,3-DIMETHYLAZETIDINIUM SALTS WITH ALKALI METAL AMIDES IN LIQUID AMMONIA [J].

ANDERSON, AG ;

WILLS, MT .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (08) :3046-&

[3]

BECKWITH AL, 1974, TETRAHEDRON LETT, P2251

[4] EFFECT OF NON-BONDED INTERACTIONS ON THE REGIOSELECTIVITY OF CYCLIZATION OF THE HEX-5-ENYL RADICAL [J].

BECKWITH, ALJ ;

LAWRENCE, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (11) :1535-1539

[5] ATOM TRANSFER CYCLIZATION REACTIONS OF ALPHA-IODO ESTERS, KETONES, AND MALONATES - EXAMPLES OF SELECTIVE 5-EXO, 6-ENDO, 6-EXO, AND 7-ENDO RING CLOSURES [J].

CURRAN, DP ;

CHANG, CT .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3140-3157

[6] Synthesis of bridgehead nitrogen heterocycles via cyclization of α-ammonio 5-hexenyl radicals [J].

Della, EW ;

Smith, PA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (06) :1798-1806

[7] THE DIRECTED PAUSON-KHAND REACTION [J].

KRAFFT, ME ;

JULIANO, CA ;

SCOTT, IL ;

WRIGHT, C ;

MCEACHIN, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1693-1703

[8] RADICAL CYCLIZATION AS AN APPROACH TOWARD THE SYNTHESIS OF PYRROLIDINES [J].

PADWA, A ;

NIMMESGERN, H ;

WONG, GSK .

TETRAHEDRON LETTERS, 1985, 26 (08) :957-960

[9] SYNTHESIS OF THE PYRROLIDINE RING-SYSTEM BY RADICAL CYCLIZATION [J].

PADWA, A ;

NIMMESGERN, H ;

WONG, GSK .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5620-5627

[10]

PORTER NA, 1978, ACS S SERIES, V69, pCH6

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