CYCLIZATION OF DEPROTONATED 2-PHENYL-1-TOSYLAZIRIDINE - A SURPRISING EXAMPLE OF AN INTRAMOLECULAR NUCLEOPHILIC AROMATIC ADDITION

被引：33

作者：

BRETERNITZ, HJ

SCHAUMANN, E

ADIWIDJAJA, G

机构：

[1] TECH UNIV CLAUSTHAL,INST ORGAN CHEM,W-3392 CLAUSTHAL ZELLERFE,GERMANY

[2] UNIV HAMBURG,INST MINERAL PETROG,W-2000 HAMBURG 13,GERMANY

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(00)79650-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deprotonation of 2-phenyl-1-tosylaziridine 1 with butyl lithium gives an anion that cyclizes to 4 by an intramolecular nucleophilic aromatic addition. Treatment of derivatives 5, 6 with a Grignard reagent produces aziridines 10, 11.

引用

页码：1299 / 1302

页数：4

共 4 条

[1] BRETERNITZ HJ, IN PRESS
[2] ACTIVATED AZIRIDINES .I. REACTION OF ANILINES WITH O-ETHYL-N,N-ETHYLENEURETHANE . MECHANISM + HAMMETT RHO-CONSTANT
HAM, GE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (10) : 3052 - &
[3] RING-OPENING OF OXIRANES BY SILYL-SUBSTITUTED ALLYL ANIONS - A REGIOCHEMICAL CHAMELEON
SCHAUMANN, E
KIRSCHNING, A
[J]. TETRAHEDRON LETTERS, 1988, 29 (34) : 4281 - 4284
[4] CRYSTAL AND MOLECULAR STRUCTURE OF 7-(P-IODOBENZENESULFONYL)-7-AZABICYCLO 4.1.0 HEPTANE
TREFONAS, LM
MAJESTE, R
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1965, 2 (01) : 80 - &

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