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2,3,4‐Triphenyl‐3‐azabicyclo[3.2.0]hepta‐1,4‐diene − Facile Ring‐Opening by Electrophiles and Novel Reactions with Dimethyl Acetylenedicarboxylate
Author(s) -
Matsumoto Kiyoshi,
Goto Sadahito,
Hayashi Naoto,
Iida Hirokazu,
Uchida Takane,
Kakehi Akikazu
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400433
Subject(s) - dimethyl acetylenedicarboxylate , chemistry , azepine , cyclobutene , electrophile , moiety , substituent , ring (chemistry) , diene , dilithium , cycloaddition , medicinal chemistry , stereochemistry , organic chemistry , catalysis , deprotonation , natural rubber , ion
A 3‐azabicyclo[3.2.0]hepta‐1,4‐diene with no substituent in the cyclobutene moiety has been prepared for the first time; it undergoes extremely facile electrophilic attack at the β‐position to give the ring‐opened product, probably by a retro‐Friedel−Crafts process. The title compound also undergoes a novel reaction with dimethyl acetylenedicarboxylate to afford the azepine. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)