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.

引用

页码：6851 / 6855

页数：5

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