Aza-pinacol rearrangement: acid-catalyzed rearrangement of aziridines to imines

被引：42

作者：

Sugihara, Y ^{[1
]}

Iimura, S ^{[1
]}

Nakayama, J ^{[1
]}

机构：

[1] Saitama Univ, Dept Chem, Fac Sci, Saitama 3388570, Japan

来源：

CHEMICAL COMMUNICATIONS | 2002年 / 02期

关键词：

D O I：

10.1039/b109445a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of di-, tri-, and tetra-substituted N-tosylaziridines [N-(toluene-p-sulfonyl) aziridines] 1, prepared by aziridination of the corresponding alkenes with N-[(tolyl-p-sulfonyl) imino] phenyliodinane (TsN = IPh), was found to undergo a BF3-catalyzed rearrangement (aza-pinacol rearrangement) under mild conditions to give the corresponding N- tosylimines 2 generally in satisfactory yields.

引用

页码：134 / 135

页数：2

共 50 条

[21] Understanding the mechanism of the chiral phosphoric acid-catalyzed aza-Cope rearrangement
Falcone, Bruno N.
Grayson, Matthew N.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (16) : 3656 - 3664
[22] ACID-CATALYZED NITRAMINE REARRANGEMENT .6. DIVERSION OF REARRANGEMENT
WHITE, WN
WHITE, HS
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06): : 1803 - &
[23] TRIFLUOROMETHANESULFONIC ACID-CATALYZED REARRANGEMENT OF HOMOADAMANTANE
TAKAISHI, N
INAMOTO, Y
FUJIKURA, Y
AIGAMI, K
GOLICNIK, B
MLINARICMAJERSKI, K
MAJERSKI, Z
OSAWA, E
SCHLEYER, PV
CHEMISTRY LETTERS, 1976, (07) : 763 - 768
[24] Investigation of the acid-catalyzed rearrangement of morphinans
Csutoras, Csaba
Berenyi, Sandor
Neumeyer, John L.
LETTERS IN ORGANIC CHEMISTRY, 2007, 4 (06) : 409 - 413
[25] ACID-CATALYZED REARRANGEMENT OF LAURINTEROL DERIVATIVES
SUZUKI, M
HAYAKAWA, Y
IRIE, T
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1969, 42 (11) : 3342 - +
[26] ACID-CATALYZED REDOX REARRANGEMENT OF A HEMIKETAL
LEMEN, J
ZECHES, M
SIGAUT, F
HETEROCYCLES, 1982, 19 (10) : 1807 - 1812
[27] THE ACID-CATALYZED REARRANGEMENT OF THE STILBENE OXIDES
HOUSE, HO
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (11) : 3070 - 3075
[28] Acid-catalyzed rearrangement of ethynylcycloheptatriene to phenylallene
Kitagawa, T
Kamada, J
Minegishi, S
Takeuchi, K
ORGANIC LETTERS, 2000, 2 (19) : 3011 - 3013
[29] LEWIS ACID-CATALYZED REARRANGEMENT OF TRITERPENOIDS
CHATTERJEE, A
MUKHOPADHYAY, S
CHATTOPADHYAY, K
TETRAHEDRON, 1976, 32 (24) : 3051 - 3053
[30] ACID-CATALYZED REARRANGEMENT OF A DITERPENOID EPOXIDE
MURRAY, RDH
MILLS, RW
MCALEES, AJ
MCCRINDLE, R
TETRAHEDRON, 1974, 30 (18) : 3399 - 3405

← 1 2 3 4 5 →