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Cu-promoted [2 + 2] cycloaddition of 1,4-bisallenes.

Authors :
Kitagaki S
Kajita M
Narita S
Mukai C
Source :
Organic letters [Org Lett] 2012 Mar 16; Vol. 14 (6), pp. 1366-9. Date of Electronic Publication: 2012 Feb 24.
Publication Year :
2012

Abstract

The thermal reaction of 1,4-bisallenes with the aid of Cu salt/amine significantly suppressed the formal [3,3] sigmatropic rearrangement resulting in the highly selective formation of the bicyclo[4.2.0]octadiene framework. This reaction could be applied to the one-pot synthesis of bicyclo[4.2.0]octadienes from 1,5-hexadiynes via the Crabbé homologation.

Subjects

Subjects :
Alkadienes chemistry
Amines chemistry
Bridged Bicyclo Compounds chemistry
Catalysis
Cyclization
Molecular Structure
Salts chemistry
Alkadienes chemical synthesis
Alkynes chemistry
Bridged Bicyclo Compounds chemical synthesis
Copper chemistry

Details

Language :
English
ISSN :
1523-7052
Volume :
14
Issue :
6
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
22364480
Full Text :
https://doi.org/10.1021/ol300096u
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