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Cyclopropyl Building Blocks for Organic Synthesis, 36.Unprecedented Addition of Dialkoxycarbenes to Tetrasubstituted Alkenes: Bicyclopropylidene and 2‐Chlorocyclopropylideneacetate

 

作者: Armin de Meijere,   Sergei I. Kozhushkov,   Dmitry S. Yufit,   Roland Boese,   Thomas Haumann,   David L. Pole,   Pradeep K. Sharma,   John Warkentin,  

 

期刊: Liebigs Annalen  （WILEY Available online 1996）
卷期: Volume 1996, issue 4  

页码: 601-612

 

ISSN:0947-3440

 

年代: 1996

 

DOI:10.1002/jlac.199619960421

 

出版商: WILEY‐VCH Verlag

 

关键词: Δ3‐1,3,4‐Oxadiazolines;Dialkoxycarbenes;Bicyclopropylidene;Dispiro[2.0.2.1]heptanes

 

数据来源: WILEY

 

摘要:

AbstractThe cycloaddition reactions of several dialkoxycarbenes generated in situ from the corresponding 2,2‐dialkoxy‐Δ3‐1,3,4‐oxadiazolines of the type3with bicyclopropylidene1afford the dialkyl acetals of dispiro[2.0.2.1]heptane‐7‐one (4), whereas the analogous addition to methyl (1‐chloromethylene‐1‐carboxylate)cyclopropane26leads to the formation of a complex mixture of products. Those products can best be rationalized in terms of nucleophilic attack of the dialkoxycarbene on the strained CC double bond, to form a dipolar intermediate capable of a variety of intramolecular rearrangements. Several chemical transformations of the compounds of

 

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