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Transannular reactions of two non-parallel 1,3-butadiyne units: syntheses, structures and protonation reactions of 1-isopropyl-1-azacyclopentadeca-3,5,11,13-tetrayne and 1-isopropyl-1-azacyclohexadeca-3,5,12,14-tetrayne

The syntheses of 1-isopropyl-1-azacyclopentadeca-3,5,11,13-tetrayne (15a) and 1-isopropyl-1-azacyclohexadeca-3,5,12,14-tetrayne (15b) were accomplished in a stepwise approach. The key intermediates were 1,14-dibromotetradeca-2,4,10,12-tetrayne (14a) and 1,15-dibromopentadeca-2,4,11,13-tetrayne (14b)...

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Bibliographic Details
Main Authors: Schmidt, Erik M. (Author) , Gleiter, Rolf (Author) , Rominger, Frank (Author)
Format: Article (Journal)
Language:English
Published: 15 June 2004
In: European journal of organic chemistry
Year: 2004, Issue: 13, Pages: 2818-2825
ISSN:1099-0690
DOI:10.1002/ejoc.200400088
Online Access:Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/ejoc.200400088
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200400088
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Author Notes:Erik M. Schmidt, Rolf Gleiter, and Frank Rominger
Description
Summary:The syntheses of 1-isopropyl-1-azacyclopentadeca-3,5,11,13-tetrayne (15a) and 1-isopropyl-1-azacyclohexadeca-3,5,12,14-tetrayne (15b) were accomplished in a stepwise approach. The key intermediates were 1,14-dibromotetradeca-2,4,10,12-tetrayne (14a) and 1,15-dibromopentadeca-2,4,11,13-tetrayne (14b). The ring closure to 15a and 15b was achieved by reaction with isopropylamine. X-ray investigations on single crystals of 15a and 15b revealed a non-parallel orientation of the 1,3-butadiyne units. The reaction of 15b with concd. HCl in ethanol yielded 5,12-dichloro-2-isopropyl-1,2,3,6,7,8,9,10-octahydrocyclonona[e]isoindole (16c) and 5-chloro-2-isopropyl-2,3,6,7,8,9,10,11-octahydrocyclonona[e]isoindol-12(1H)-one (17c). A mechanism for the reaction of 15b with HCl is proposed. The reaction of 15a with concd. HCl in ethanol gives 5-chloro-2-isopropyl-2,3,7,8,9,10-hexahydrocycloocta[e]isoindol-11(6H)-one (24c). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Item Description:Gesehen am 27.10.2020
Physical Description:Online Resource
ISSN:1099-0690
DOI:10.1002/ejoc.200400088

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