High pressure-promoted [2+2] cycloaddition reactions of 4-methylphenyl 1,2-propadienyl sulfone with enol ethers

被引:16
作者
Aben, RWM
Braverman, S
Scheeren, HW
机构
[1] Catholic Univ Nijmegen, Dept Organ Chem, NSR Ctr, NL-6525 ED Nijmegen, Netherlands
[2] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel
关键词
allenes; 1-alkoxybuta-1,3-dienes; 3-alkoxymethylene cyclobutanes; cycloadditions; high-pressure chemistry; regioselectivity;
D O I
10.1002/ejoc.200390135
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Under high pressure conditions, 4-methylphenyl 1,2-propadienyl sulfone (1) and enol ethers (6) undergo regioselective [2+2] cycloaddition reactions to give (3-alkoxycyclobutylidenennethyl 4-methylphenyl sulfones (7). The cycloaddition reaction has a broad scope with respect to the substituents allowed at the enol ether. The synthetic potential of the obtained cycloadducts is illustrated by a stereoselective addition of dimethylamine to the double bond of 7a and 7b to yield 11a and 11b and by a tertiary amine-induced double bond isomerisation of 7a and 7b, followed by ring-opening of the cyclobutene intermediate to yield 1-alkoxybuta-1,3-dienes 12a and 12b. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
引用
收藏
页码:894 / 897
页数:4
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