ChemInform Abstract: THE SYNTHESIS OF PENTATRIDECA‐, PENTAPENTADECA‐, PENTAHEPTADECA‐, AND PENTANONADECAFULVALENE DERIVATIVES

Abstract

In literaturbekannter Weise werden durch Kupplung entsprechender Annulenone mit Natrium‐cyclopentadienid die Fulvalene (I)‐(IV) hergestellt.

Synthesis of derivatives of aza[14]annulene, aza[16]annulene, aza[18]annulene, aza[20]annulene, and aza[22]annulene, diatropic and paratropic vinylogues of pyridine

“…5,6,7,8-Tetradehydro-1 5H-dibenzo[a,g]cyclotridecen-1 5-one Oxime (13).-A suspension of the ketone (12)8 (830 mg, 2.96 mmol) in methanol (90 ml) and T H F (40 ml) was stirred and warmed to 3 5 4 °C and a solution of hydroxylamine hydrochloride (1.90 g, 27.3 mmol) in water (10 ml) was then added in one portion. The mixture was stirred for 3 h at the same temperature after which it was poured into water and the precipitate filtered off to afford the oxime (13) (14).-Phosphorus pentachloride (322 mg, 1.55 mmol) was added in one portion to an ice-cooled, stirred solution of the oxime (13) (91.3 mg, 0.301 mmol) in dry T H F (40 ml) and the solution was allowed to rise to room temperature; it was then stirred overnight. After being stirred for a further 4 h at 4 0 -4 5 "C, the solution was poured into water and the mixture warmed to 40°C on a steam-bath.…”