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1,3‐Dipolar cycloadditions of 9‐diazofluorenes and diphenyldiazomethane to 2‐acyl‐2 H ‐1,2,3‐diazaphospholes
Author(s) -
Guo Xiangyun,
Feng Li,
Wang Quanrui,
Li Zhiming,
Tao Fenggang
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430215
Subject(s) - chemistry , moiety , cycloaddition , 1,3 dipolar cycloaddition , bicyclic molecule , adduct , medicinal chemistry , nitrogen , stereochemistry , nitrone , dipole , organic chemistry , catalysis
A series of 2‐acyl‐2 H ‐1,2,3‐diazaphospholes 3 underwent ready 1,3‐dipolar cycloaddition reactions with 9‐diazofluorenes as the 1,3‐dipole, yielding the respective bicyclic phosphiranes 5 or trimers 7 depending on the reaction conditions employed. The reaction is believed to proceed via the formation of the [3+2]‐cycloaddition adducts followed by elimination of nitrogen from the cyclic azo moiety. In the case of 3c , the phosphatetraazabicyclooctadiene compound 6 has been isolated with no loss of nitrogen. Likewise, the dipolar cycloaddition reaction of diphenyldiazomethane with the >CP‐ moiety as the 1,3‐dipolarophile gave phosphadiazabicyclohexenes 8 in 32–68% yields.