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Cycloaddition behavior of 3,4‐diazacyclopentadienone dioxides toward bicyclo[2.2.1]heptadiene derivatives. X‐ray analysis of the cycloadduct and reaction pathway
Author(s) -
Eto Masashi,
Harano Kazunobu,
Yoshitake Yasuyuki,
Hisano Takuzo
Publication year - 1993
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.5570300618
Subject(s) - cycloaddition , chemistry , 1,3 dipolar cycloaddition , bicyclic molecule , naphthalene , norbornadiene , computational chemistry , stereospecificity , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The cycloaddition behavior of 2,5‐disubstituted 3,4‐diazacyclopentadienone dioxide 1a‐c toward epoxy‐naphthalene ( 2a ) and norbornadiene ( 2b ) was investigated. The structures of the products were determined on the basis of the 1 H‐ and 13 C‐nmr spectral data and the X‐ray analysis data. The stereospecific formation of the endo‐exo 1,3‐dipolar cycloadducts from 2a indicates that the cycloadduct resulted from the direct 1,3‐dipolar cycloaddition. The cycloaddition behavior of 1 toward 2 is discussed on the basis of the PM3‐calculated transition‐state structures.