2,3,4‐Triphenyl‐3‐azabicyclo[3.2.0]hepta‐1,4‐diene − Facile Ring‐Opening by Electrophiles and Novel Reactions with Dimethyl Acetylenedicarboxylate | Zendy

Matsumoto Kiyoshi | Zendy; Goto Sadahito | Zendy; Hayashi Naoto | Zendy; Iida Hirokazu | Zendy; Uchida Takane | Zendy; Kakehi Akikazu | Zendy

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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)

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