Synthesis and Structural Properties of Bridged 1,8-Diazacyclotetradeca-4,11-diynes

✍ Scribed by Volker Wolfart; Rolf Gleiter; Hermann Irngartinger; Thomas Oeser; Claus Krieger

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 186 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199812)1998:12<2803::aid-ejoc2803>3.0.co;2-c

✦ Synopsis

The synthesis of 1,8-diazacyclotetradeca-4,11-diyne (4) was diisopropyl-1,8-diazacyclotetradeca-4,11-diyne (13a), as well as of 14, 24, 27 and 31 were studied by means of the X-ray accomplished by reaction of 1,6-dibromo-3-hexyne (11) with ammonia. Similarly, the preparation of 1-azacyclotetradeca-technique. It was found that 13a adopts a chair-like conformation (C 2h ) with an equatorial orientation of the 4,11-diyne (5) was achieved from 1,13-dibromotrideca-3,11diyne (10) and ammonia. The reaction of α,ω-diamines of isopropyl groups. In 14, 24, 27, and 31 the 14-membered rings adopt a twist-boat conformation. The distance between linear hydrocarbons of the chain length C 4 to C 10 with 11 yielded the corresponding bicyclic diynes 23-29. The the nitrogen atoms varies between 4.662(2) and 5.189(2) A ˚.

In the case of 14, 24 and 27 the nitrogen atoms are reaction of 4 with 11 yielded 1,8-diazabicyclo[6.6.6]icosa-4,11,16-triyne ( ). Similarly, the reaction of 4 with 1,4-pyramidalized and point inside the cage while in 31 the substituents at each nitrogen atom and the nitrogen atoms dibromo-2-butyne yielded 1,8-diazabicyclo[6.6.4]octadeca-4,11,16-triyne (31). The molecular structures of 1,8-are situated in one plane.