Photosensitized regeneration of carbonyl compounds from oximes

被引：41

作者：

de Lijser, HJP ^{[1
]}

Fardoun, FH ^{[1
]}

Sawyer, JR ^{[1
]}

Quant, M ^{[1
]}

机构：

[1] Calif State Univ Fullerton, Dept Chem & Biochem, Fullerton, CA 92834 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 14期

关键词：

D O I：

10.1021/ol025978a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Deprotection of oximes to their corresponding carbonyl compounds through the use of photosensitized electron-transfer reactions proceeds in reasonable to good yields. Better yields are obtained in nonpolar solvents and when triplet sensitizers are used. Preliminary mechanistic studies suggest the involvement of an iminoxyl radical.

引用

页码：2325 / 2328

页数：4

共 26 条

[1]

AMIN JH, 1963, TETRAHEDRON LETT, P1585

[2] Anodic behaviour of aromatic oximes: an electrochemical deoximation reaction [J].

Bencharif, L ;

Tallec, A ;

Tardivel, R .

ELECTROCHIMICA ACTA, 1997, 42 (23-24) :3509-3512

[3] PREPARATIVE CONVERSION OF OXIMES TO PARENT CARBONYL COMPOUNDS BY CERIUM(4) OXIDATION [J].

BIRD, JW ;

DIAPER, DGM .

CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (01) :145-&

[4] KINETIC APPLICATIONS OF ELECTRON-PARAMAGNETIC RESONANCE SPECTROSCOPY .7. SELF-REACTIONS OF IMINOXY RADICALS [J].

BROKENSHIRE, JL ;

INGOLD, KU ;

ROBERTS, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (20) :7040-+

[5] REACTIONS OF OXIMES WITH THIANTHRENE CATION RADICAL IN NITRILE SOLVENTS - CYCLOADDITION TO FORM OXADIAZOLES AND DEOXYGENATION TO FORM NITRILES [J].

CHIOU, SS ;

HOQUE, AKMM ;

SHINE, HJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3227-3232

[6] PHOTOCHEMISTRY OF OXIMES .3. PHOTOCHEMICAL BECKMANN REARRANGEMENT [J].

CUNNINGHAM, M ;

LIM, LSN ;

JUST, G .

CANADIAN JOURNAL OF CHEMISTRY-BACK YEAR, 1971, 49 (17) :2891-+

[7]

Eisenhauer BM, 1997, J PHYS ORG CHEM, V10, P737, DOI 10.1002/(SICI)1099-1395(199710)10:10<737::AID-POC944>3.0.CO

[8]

2-N

[9] Limitations on the persistence of iminoxyls: Isolation of tert-butyl 1,1-diethylpropyl ketiminoxyl and related radicals [J].

Eisenhauer, BM ;

Wang, MH ;

Labaziewicz, H ;

Ngo, M ;

Mendenhall, GD .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :2050-2053

[10] Iminoxyl radicals and stable products from the one-electron oxidation of 1-methylindole-3-carbaldehyde oximes [J].

Everett, SA ;

Naylor, MA ;

Stratford, MRL ;

Patel, KB ;

Ford, E ;

Mortensen, A ;

Ferguson, AC ;

Vojnovic, B ;

Wardman, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (10) :1989-1997

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