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Über 1,2‐Umlagerungen und CH‐Einschubreaktionen Acyclischer Alkylidencarbene

 

作者: Bernd Ondruschka,   Matthias Remmler,   Gerhard Zimmermann,   Christian Krüger,  

 

期刊: Journal für Praktische Chemie  (WILEY Available online 1987)
卷期: Volume 329, issue 1  

页码: 49-54

 

ISSN:0021-8383

 

年代: 1987

 

DOI:10.1002/prac.19873290107

 

出版商: WILEY‐VCH Verlag GmbH

 

数据来源: WILEY

 

摘要:

On 1.2‐Shift Reactions and CH‐Insertions of Acyclic Alkylidene CarbenesTwo series of acyclic terminal vinyl bromides (1…4and5…7) were tested in the reaction with potassium tert‐butoxide as precursors of alkylidene carbenes. As expected1up to4only give 1‐alkynes whereas the 2‐methylated vinyl bromides5,6and7yield 1‐methylated cyclopentenes predominantly besides 2‐alkynes. The formation of cyclopentenes indicates a reaction route via alkylidene carbenes and 1,5‐CH‐insertion reactions, that of 2‐alkynes is convincing evidence for 1,2‐alkyl shift reactions in 2‐methyl substituted alkylidene carbenes. The selectivity of 1,5‐CH‐insertion depends on the degree of alkyl substitution of the C‐5‐atom. At 240

 

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