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ChemInform Abstract: Syntheses and Structural Properties of 1,8-Diazacyclotetradeca-3,5,10,12-tetraynes.

✍ Scribed by Kirstin Hoevermann; Joachim Ritter; Frank Rominger; Bernhard Nuber; Rolf Gleiter

Publisher
John Wiley and Sons
Year
2001
Weight
26 KB
Volume
32
Category
Article
ISSN
0931-7597

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✦ Synopsis

Abstract

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The syntheses of 1,8-diazacyclotetradeca-3,5,10,12-tetrayne (2a), its N,NЈ-dimethyl (2b), N,NЈ-diethyl (2c), N,NЈ-diisopropyl (2d), N,NЈ-diallyl (2e), and N,NЈ-dibenzyl (2f) derivatives were achieved in a one-pot procedure from primary amines and 1,6-dibromo-2,4-hexadiyne (4). Diffraction studies on

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## Synthesis and Structural Properties of Bridged 1,8-Diazacyclotetradeca-4,11-diynes. -Title compounds of type (III) and (V) are synthesized as described. The molecular structures of (III), (Va), and (Vb) are determined by X-ray analysis: their 14-membered rings adopt a twist-boat conformation.

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## Abstract The synthesis of 1alkyl and 1aryl‐1‐azacyclotetradeca‐3,5,10,12‐tetraynes was achieved in a stepwise approach. The key intermediate was 1,13‐dibromotrideca‐2,4,9,11‐tetrayne (**18**). Reaction with methyl‐ (**19 a**), ethyl‐ (**19 b**), isopropyl‐ (**19 c**), __n__‐butyl‐ (**19 d**), an

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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-t