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1,3‐Dipolar cycloaddition of nitrile oxides with symmetrical tri‐ and polycyclic strained olefins
Author(s) -
Darvatkar Nitin B.,
Wankhede Karuna S.,
Bhilare Sachin V.,
Deorukhkar Amol R.,
Raut Dilip G.,
Vaidya Vipraja V.,
Trivedi Girish K.,
Salunkhe Manikrao M.
Publication year - 2010
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.421
Subject(s) - benzonitrile , chemistry , nitrile , cycloaddition , oxide , 1,3 dipolar cycloaddition , double bond , dipole , 2 norbornyl cation , computational chemistry , organic chemistry , stereochemistry , catalysis
Abstract1,3‐Dipolar cycloadditions of benzonitrile oxide and carbethoxyformonitrile oxide (CEFNO) with various facially perturbed polycyclic symmetrical dienophiles ( 1 , 1a , 1b , 2 , 2a , 2b , 3 , 3b , 4 , 5 , 6 ) were investigated. Cycloadditions took place chemoselectively at the norbornyl double bond and were found to be exclusively exo. Cycloadditions of benzonitrile oxide with dienophiles 4 and 5 led to mixture of inseparable products, however, that with CEFNO gave single products. Cycloadduct of dienophile 5 with CEFNO was found to be unstable, and it readily isomerized to more stable aromatic form. J. Heterocyclic Chem., (2010).