A novel heterocycle composed of calicene and cyclopropenone hydrazone units —3,8-bis(t-butylthio)-5,6-diazatetracyclo-[8,3,0,02,4,07,9]trideca-1,3,6,8,10,12-hexaene

✍ Scribed by Zen-ichi Yoshida; Mitsuhiro Shibata; Toyonari Sugimoto

• Book ID: 104233768
• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 192 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81401-5

✦ Synopsis

The titled compound (2) is synthesized by the reaction of 1,2-bis(dithiocyclopropenylio)cyclopentadienide with hydrazine.

The lH-and 13 C-NMR spectra suggest significant contribution of a novel polarized structure (3B) compared with a peripheral 1411 conjugation structure (3A).

--Reaction features of 3 are also examined.

Very recently we reported synthesis of a novel doubly cross-conjugated cation, 1,2-bis(dithiocyclopropenylio)cyclopentadienide (1) from 5,6-bis-(t-butylthio)calicene and 1,2-bis(t-butylthio)-3,3-dichlorocyclopropene.'

Since 1 possesses alkylthio groups of good leaving nature, it might be possible to synthesize new polycyclic a-conjugated systems by the reaction of 1 with appropriate nucleophiles.

As an example of such sort, we succeeded in synthesis of a novel polycyclic aromatic system having peripheral 1677 electrons, 3,11-bis(t-butylthio)cyclic bicalicene (2)2'3 from 1. and cyclopentadienide. This communication describes another example, that is,