Premium
A Short‐Step Synthesis of 1,6‐Methano[10]annulene‐3,4‐dicarboximides and Their Benzene‐, Naphthalene‐, and Thiophene‐Annulated Compounds
Author(s) -
Oda Mitsunori,
Nakamura Tomomi,
Neha Miyako,
Miyawaki Daisuke,
Ohta Akira,
Kuroda Shigeyasu,
Miyatake Ryuta
Publication year - 2014
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.201402776
Subject(s) - annulene , wittig reaction , chemistry , thiophene , cycloheptatriene , reagent , naphthalene , condensation , benzene , organic chemistry , medicinal chemistry , physics , thermodynamics
Triphenylphosphorane reagents 8 react with 1,3,5‐cycloheptatriene‐1,6‐dicarbaldehyde ( 2 ) under acidic as well as basic conditions to produce 1,6‐methano[10]annulene‐3,4‐dicarboximides 1 in moderate ‐to‐ good yields. The reagents 8 react with 3,4‐arene‐annulated 1,3,5‐cycloheptatriene‐1,6‐dicarbaldehydes 9 , 10 , and 11 to afford only the Wittig condensation products under acidic conditions but produce the arene‐annulated annulenedicarboximides under basic conditions. The structures of some of the dicarboximides and the intermediate Wittig condensation products were determined by X‐ray structural analysis. The emission properties of the dicarboximides were also studied.