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The synthesis of 1,2-bis(1,5,9-triazacyclododecyl)ethane: A showcase for the importance of the linker length within bis(alkylating) reagents


Medina-Molner, Alfredo; Blacque, Olivier; Spingler, Bernhard (2007). The synthesis of 1,2-bis(1,5,9-triazacyclododecyl)ethane: A showcase for the importance of the linker length within bis(alkylating) reagents. Organic Letters, 9(23):4829-4831.

Abstract

The synthesis of 1,2-bis(1,5,9-triazacyclododecyl)ethane (1) showcases how different bis(alkylating) reagents change the reaction from an intra- to an intermolecular pathway. The isolation of the intermediate hexahydro-3a,6a-ethano-1H,4H,7H,9bH-9a-aza-3a,6a-diazoniaphenalene3a,6a- diium (2) explained why initially the synthesis of 1 was not possible. Both isomers of 2 were found in solution. DFT calculations revealed that isomer 2a is 4.6 kcal/mol lower in energy than 2b. Synthesis of 1 was finally achieved by using oxalyl chloride.

Abstract

The synthesis of 1,2-bis(1,5,9-triazacyclododecyl)ethane (1) showcases how different bis(alkylating) reagents change the reaction from an intra- to an intermolecular pathway. The isolation of the intermediate hexahydro-3a,6a-ethano-1H,4H,7H,9bH-9a-aza-3a,6a-diazoniaphenalene3a,6a- diium (2) explained why initially the synthesis of 1 was not possible. Both isomers of 2 were found in solution. DFT calculations revealed that isomer 2a is 4.6 kcal/mol lower in energy than 2b. Synthesis of 1 was finally achieved by using oxalyl chloride.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:November 2007
Deposited On:23 Oct 2012 12:14
Last Modified:05 Apr 2016 16:01
Publisher:American Chemical Society
ISSN:1523-7052
Publisher DOI:https://doi.org/10.1021/ol7021627
Other Identification Number:ISI:000250673000040

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