Formation of a paratropic, dicationic 24π-electron system in D2SO4

Tetramethyloctadehydro-[26] and -[28]annulenediones have been synthesized; the corresponding dicationic species in D2SO4 showed paratropicity and diatropicity, respectively, affording the first confirmation of tropicity alternation in monocyclic annulenediones.

[1]  H. Higuchi,et al.  A methano-bridged dehydro[24]annulenedione. A highly diatropic dicationic 22π-electron species in D2SO4 , 1993 .

[2]  F. Sondheimer,et al.  Syntheses and properties of dimethylbisdehydro[15]annulenone, -[17]annulenone, -[19]annulenone, and -[21]annulenone , 1980 .

[3]  F. Sondheimer,et al.  Unsaturated macrocyclic compounds. 122. Synthesis of methyl-substituted bisdehydro[13]annulenones. Conformational isomerism and ring current effects in conjugated 13-membered cyclic ketones , 1977 .

[4]  F. Sondheimer,et al.  The synthesis of 8,13-dimethyl-2,9,11-trisdehydro[16]annulene-1,4-dione. The protonation of a [4]annulenedione to a strongly diatropic dication , 1976 .

[5]  E. Vogel,et al.  Dicarbonyl‐Derivate 1,6‐überbrückter [10]Annulene , 1971 .

[6]  F. Sondheimer.  Review Lecture - The annulenes , 1967, Proceedings of the Royal Society of London. Series A. Mathematical and Physical Sciences.

[7]  H. Higuchi,et al.  Unusual formation of a methano-bridged didehydro[20]annulenedione. A highly diatropic, dicationic 18π-electron species in D2SO4 , 1993 .

[8]  Alexandru T. Balaban,et al.  Annulenes, benzo-, hetero-, homo-derivatives and their valence isomers , 1987 .

[9]  J. Ojima,et al.  Syntheses and properties of a trimethyltetradehydro[23]annulenone and a trimethyltetradehydro[25]annulenone , 1982 .

[10]  Y. Onishi,et al.  Synthesis and properties of bisdehydro[4n+2]annulenediones , 1981 .

[11]  M. Nakagawa,et al.  Dehydroannulenes. I. Synthesis and Properties of 1,5,10,14-Tetramethyl-6,8,15,17-tetrakisdehydro[18]annulene , 1976 .

[12]  K. Yamamoto,et al.  Unsaturated macrocyclic compounds. 102. Synthesis of alkylated cyclooctadecatetraenetetrayne-1,6-diones and 1,10-diones (tetradehydro[18]annulenediones) , 1974 .