Trifluoromethylated allyl alcohols: acid-promoted reactions with arenes and unusual 'dimerization'

被引：14
|
作者：
Kazakova, Anna N. [1 ]
Iakovenko, Roman O. [1 ]
Muzalevskiy, Vasiliy M. [2 ]
Boyarskaya, Irma A. [1 ]
Avdontceva, Margarita S. [1 ]
Starova, Galina L. [1 ]
Vasilyev, Aleksander V. [1 ,3 ]
Nenajdenko, Valentine G. [2 ]
机构：
[1] St Petersburg State Univ SPbSU, Dept Organ Chem, St Petersburg 198504, Russia
[2] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119899, Russia
[3] St Petersburg State Forest Tech Univ, Dept Organ Chem, St Petersburg 194021, Russia
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 50期
关键词：
CF3-allyl alcohols; CF3-alkenes; Iron trichloride; Fluorinated indanes; CF3-allyl carbocations; ALPHA; BETA-UNSATURATED KETONES BEARING; CARBON BOND FORMATION; NUCLEOPHILIC-SUBSTITUTION; ELECTROPHILIC ADDITION; ALKYLATION; CARBOCATIONS; FLUORINE; INDOLES; CHEMISTRY; CHARACTER;
D O I：
10.1016/j.tetlet.2014.10.083
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unusual 'dimerization' of CF3-allyl alcohols [ArCH=CHCH(OH)CF3] under the action of anhydrous FeCl3 was found to give fluorinated indanes in 62-90% yields via the formation of intermediate allyl cations. Reactions of CF3-allyl alcohols with arenes (Ar'H) led to CF3-alkenes [Ar(Ar')CHCH=CHCF3] in 48-75% yields. The mechanisms of the transformations are discussed. (C) 2014 Elsevier Ltd. All rights reserved.
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页码：6851 / 6855
页数：5
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