The Schenck rearrangement of allylic hydroperoxides

被引：22
作者：
Davies, Alwyn G. [1 ]
机构：
[1] UCL, Dept Chem, London WC1H 0AJ, England
来源：
JOURNAL OF CHEMICAL RESEARCH | 2009年 / 09期
关键词：
allyl hydroperoxides; allylperoxyl radicals; autoxidation; mechanism; Schenck rearrangement; Smith rearrangement; ZUR PHOTOSENSIBILISIERTEN AUTOXYDATION; SINGLET-OXYGEN; ENE REACTION; MECHANISM; AUTOXIDATION; CHOLESTEROL; STEREOSELECTIVITY; CYCLIZATION; OXIDATION; PEROXIDE;
D O I：
10.3184/030823409X12491375725131
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
It is 50 years since Schenck's discovery of the ubiquitous rearrangement of allylic hydroperoxides, and its unique homolytic mechanism has now been clarified by a combination of experimental and computational methods. The recognised examples of the reaction are surveyed and the way in which the present mechanistic picture has emerged is reviewed. A brief account is given of the closely related Smith epimerisation of allylic hydroperoxides.
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页码：533 / 544
页数：12
相关论文
共 53 条
[1]  
Alfassi Z., 1997, PEROXYL RADICALS
[2]   STEREOSELECTIVITY IN THE FORMATION AND ALLYLIC REARRANGEMENT OF 8A-METHYL-1,2,3,4,4A,7,8,8A-OCTAHYDRONAPHTHALENYL AND 8A-ETHYL-1,2,3,4,4A,7,8,8A-OCTAHYDRONAPHTHALENYL HYDROPEROXIDES [J].
AVILA, DV ;
DAVIES, AG ;
DAVISON, IGE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1988, (10) :1847-1852
[3]   Theoretical investigation of linalool oxidation [J].
Backtorp, Carina ;
Wass, J. R. Tobias Johnson ;
Panas, Itai ;
Skold, Maria ;
Borje, Anna ;
Nyman, Gunnar .
JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (44) :12204-12212
[4]   Mechanism of air oxidation of the fragrance terpene geraniol [J].
Baecktorp, Carina ;
Hagvall, Lina ;
Boerje, Anna ;
Karlberg, Ann-Therese ;
Norrby, Per-Ola ;
Nyman, Gunnar .
JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2008, 4 (01) :101-106
[5]   THE MECHANISMS OF THE REARRANGEMENTS OF ALLYLIC HYDROPEROXIDES [J].
BECKWITH, ALJ ;
DAVIES, AG ;
DAVISON, IGE ;
MACCOLL, A ;
MRUZEK, MH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (07) :475-476
[6]   THE MECHANISMS OF THE REARRANGEMENTS OF ALLYLIC HYDROPEROXIDES - 5-ALPHA-HYDROPEROXY-3-BETA-HYDROXYCHOLEST-6-ENE AND 7-ALPHA-HYDROPEROXY-3-BETA-HYDROXYCHOLEST-5-ENE [J].
BECKWITH, ALJ ;
DAVIES, AG ;
DAVISON, IGE ;
MACCOLL, A ;
MRUZEK, MH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (07) :815-824
[7]   A THEORETICAL INVESTIGATION OF THE 1,3-MIGRATION IN ALLYLPEROXYL RADICALS [J].
BOYD, SL ;
BOYD, RJ ;
SHI, Z ;
BARCLAY, LRC ;
PORTER, NA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (02) :687-693
[8]   ISOLATION AND REARRANGEMENT OF PURE ACYCLIC ALLYLIC HYDROPEROXIDES [J].
BRILL, WF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (14) :3286-&
[9]   THE ALLYLIC REARRANGEMENT OF HYDROPEROXIDES - THE ALLYLPEROXYL RADICAL [J].
BRILL, WF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (04) :621-627
[10]   THE FORMATION AND SUBSEQUENT CYCLIZATION OF NOVEL HYDROPEROXIDES FROM A 1,4-DIENE AND A 1,5-DIENE [J].
CARLESS, HAJ ;
BATTEN, RJ .
TETRAHEDRON LETTERS, 1982, 23 (45) :4735-4738
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