NEW ACCESS TO DI-EXO-METHYLENECYCLOBUTANES VIA [2+2] CYCLOADDITION OF 3-METHYLTHIO-4-TRIMETHYLSILYL-1,2-BUTADIENE WITH ALKENES MEDIATED BY A LEWIS-ACID

被引:36
作者
HOJO, M [1 ]
TOMITA, K [1 ]
HIROHARA, Y [1 ]
HOSOMI, A [1 ]
机构
[1] UNIV TSUKUBA,DEPT CHEM,TSUKUBA,IBARAKI 305,JAPAN
关键词
2 + 2] CYCLOADDITION; ALLENYLMETHYLSILANE; 1,2,3-BUTATRIENE; DI-EXO-METHYLENECYCLOBUTANE; ALLENYL SULFIDE; 4+3] CYLOADDITION;
D O I
10.1016/S0040-4039(00)61469-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methylthio-substituted allenylmethylsilane, a kind of allylsilane, undergoes only [2 + 2] cycloaddition reaction with alkenes mediated by a Lewis acid to afford the corresponding methylenecyclobutanes which are readily converted to di-exo-methylenecyclobutanes by rite sequential oxidation-1,2-elimination in good yield. Di-exo-methylenecyclobutane is also successfully applied to construct a bicyclo[5.2.0]nonenone skeleton by the reaction with 2-oxyallyl cation.
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页码:8123 / 8126
页数:4
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