Theoretical studies on cycloaddition reactions between 2-azoniaallene cations and olefins

Si-Ya Yang; Cheng-Ke Sun; De-Cai Fang

doi:10.1021/jo025575o

Theoretical studies on cycloaddition reactions between 2-azoniaallene cations and olefins

J Org Chem. 2002 May 31;67(11):3841-6. doi: 10.1021/jo025575o.

Authors

Si-Ya Yang¹, Cheng-Ke Sun, De-Cai Fang

Affiliation

¹ Department of Chemistry, Beijing Normal University, Beijing 100875, China.

PMID: 12027701
DOI: 10.1021/jo025575o

Abstract

The mechanisms of cycloaddition reactions between 2-azoniaallene cations and olefins have been explored at the B3LYP/6-31G level. It is found that the positive charge in 2-azoniaallene makes the reaction more complicated. For the reactions between olefins with Cl groups or CH(3) groups and 2-azoniaallene, the typical carboniums have been located along the reaction path. In addition, for the reactions between 1,1-dimethylethene and 1,3-dichrolo-2-azoniaallene, different paths and products have been rationalized and verified.