The intermediacy of oxycyclobutenes in the synthesis and reactions of cyclobutenones and cyclobutenols

被引：7

作者：

Frimer, AA ^{[1
]}

Pizem, H ^{[1
]}

机构：

[1] Bar Ilan Univ, Dept Chem, Ethel & David Chair Act Oxygen Chem, IL-52900 Ramat Gan, Israel

来源：

TETRAHEDRON | 1999年 / 55卷 / 41期

关键词：

cyclobutenes; rearrangements; oxygen; singlet; Wittig reactions;

D O I：

10.1016/S0040-4020(99)00695-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinylcyclobutenol 7, generated via the singlet oxygenation of alkylidenecyclobutene 5, rearranges at room temperature to a solvent dependent mixture of isomeric dienones 10 and 11. Alkylidenecyclobutene 5 was prepared in turn via an inverse Wittig addition of the isopropyl ylide to cyclobutenone 4; in a normal addition of ketone to ylide, vinylallene 12 is also obtained. Finally, the corresponding Wittig reaction of 4,4-dichlorocyclobutenone 3 yields only the 2,4-dichloro isomer 13. When this reaction is carried in the presence of n-butoxide, dienone 32 is generated. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：12175 / 12186

页数：12

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