A new method for the generation and cyclization of iminyl radicals via the Hudson reaction

被引：51

作者：

Lin, XC ^{[1
]}

Stien, D ^{[1
]}

Weinreb, SM ^{[1
]}

机构：

[1] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 04期

关键词：

D O I：

10.1021/ol990720e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild new synthetic procedure has been developed for in situ generation and cyclization of iminyl radicals onto pendant alkenes, followed by functionalization of the resulting carbon radical by one of a variety of trapping reagents, The key process in the method involves production of the iminyl radical via treatment of an aldoxime or ketoxime with readily available 2,6-dimethylbenzenesulfinyl chloride at -50 degrees C to room temperature (Hudson reaction).

引用

页码：637 / 639

页数：3

共 20 条

[1] RECENT PROGRESS IN THE USE OF SULFONYL RADICALS IN ORGANIC-SYNTHESIS - A REVIEW
BERTRAND, MP
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1994, 26 (03) : 257 - 290
[2] BLEEKER IP, 1979, J R NETH CHEM SOC, P121
[3] A new method for the generation and capture of iminyl radicals
Boivin, J
Schiano, AM
Zard, SZ
Zhang, HW
[J]. TETRAHEDRON LETTERS, 1999, 40 (24) : 4531 - 4534
[4] IMINYL, AMIDYL, AND CARBAMYL RADICALS FROM O-BENZOYL OXIMES AND O-BENZOYL HYDROXAMIC ACID-DERIVATIVES
BOIVIN, J
CALLIERDUBLANCHET, AC
QUICLETSIRE, B
SCHIANO, AM
ZARD, SZ
[J]. TETRAHEDRON, 1995, 51 (23) : 6517 - 6528
[5] IMINYL RADICALS .3. FURTHER SYNTHETICALLY USEFUL SOURCES OF IMINYL RADICALS
BOIVIN, J
FOUQUET, E
SCHIANO, AM
ZARD, SZ
[J]. TETRAHEDRON, 1994, 50 (06) : 1769 - 1776
[6] N-TERT-BUTYLSULFONYLCARBAMATES FROM TERT-BUTYLSULFINYL CHLORIDE AND N-HYDROXYCARBAMATES - REACTION-MECHANISM AND OBSERVATION OF CIDNP
BOUMA, WJ
ENGBERTS, JBFN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (01) : 143 - 145
[7] Cyclisation of aminyl radicals derived from amino acids
Bowman, WR
Broadhurst, MJ
Coghlan, DR
Lewis, KA
[J]. TETRAHEDRON LETTERS, 1997, 38 (35) : 6301 - 6304
[8] REACTION BETWEEN OXIMES AND SULFINYL CHLORIDES - READY, LOW-TEMPERATURE RADICAL REARRANGEMENT PROCESS
BROWN, C
HUDSON, RF
RECORD, KAF
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (08): : 822 - 828
[9] A NEW SOURCE OF NITROGEN CENTERED RADICALS
CALLIERDUBLANCHET, AC
QUICLETSIRE, B
ZARD, SZ
[J]. TETRAHEDRON LETTERS, 1995, 36 (48) : 8791 - 8794
[10] CEVASCO G, 1990, GAZZ CHIM ITAL, V120, P131

← 1 2 →