Thianthrene as a source of the 1,2-benzene dianion

被引：18

作者：

Yus, M ^{[1
]}

Foubelo, F ^{[1
]}

Ferrández, JV ^{[1
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 40期

关键词：

heterocycle reductive opening; DTBB-catalysed lithiation; dianionic synthon; cyclisation;

D O I：

10.1016/S0040-4039(02)01661-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The lithiation of thianthrene 1 with lithium and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB, 4% molar) in THF at -90degreesC, followed by reaction with a carbonyl compound [Bu'CHO, Me2CO, Et2CO, (CH2)(5)CO] at the same temperature, gives an intermediate, which was lithitated again and reacted with a second carbonyl compound [Bu'CHO, PhCHO, Ph(CH2)(2)CHO, Me2CO, Et2CO, (CH2)(5)CO] to give, after the final hydrolysis, the expected diols 2. Compounds 2 are easily cyclised under acidic conditions (85% H3PO4) to yield the expected phthalans in almost quantitative yields. Finally, when after the reaction with the first carbonyl compound (PhCHO, Me2CO), carbon dioxide was used as the second electrophile, the expected substituted phthalides 3 were obtained after acidic work-up. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：7205 / 7207

页数：3

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