The Journal of Organic Chemistry

Regiospecific synthesis of 3, 4-disubstituted furans. 7. Synthesis and reactions of 3, 4-bis (trimethylsilyl) furan: Diels-Alder cycloaddition, Friedel-Crafts acylation, and …

ZZ Song, MS Ho, HNC Wong

Index: Song, Zhi Zhong; Ho, Mei Sing; Wong, Henry N. C. Journal of Organic Chemistry, 1994 , vol. 59, # 14 p. 3917 - 3926

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Citation Number: 36

Abstract

As a versatile building block, 3, 4-bis (trimethylsilyl) furan (l), conveniently obtained through a Diels-Alder reaction between 4-phenyloxazole and bisttrimethylsilyl) acetylene, was able to undergo Diels-Alder cycloadditions with dienophiles. In two separate experiments, extrusion of bis (trimethylsily1)-acetylene occurred when 1 was treated with acetylenic dienophiles. Furan 1 was also found to undergo Friedel-Crafts acylations at the ...

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