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Naphtho[2,3‐ d ] [1,2,3]oxadiazole
Author(s) -
Blocher Achim,
Zeller KlausPeter
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199114761
Subject(s) - oxadiazole , deprotonation , quinone , naphthalene , chemistry , salt (chemistry) , molecule , medicinal chemistry , stereochemistry , organic chemistry , ion
Not the o ‐quinone diazide 1 but the title molecule 3 results from the deprotonation of diazonium salt 2 . Compound 3 is the first preparatively realized example of a 1,2,3‐oxadiazole. The high likelihood of the formation of 3 is probably due to the destabilization of the o ‐quinone and o ‐quinone bismethide structures in 1 , which are passed over in favor of the lower energy naphthalene unit in the transformation to 3 .