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Degradation of Dichloromethane by Bispidine

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons58499

Cui,  Huiling
Research Group Pörschke, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58578

Goddard,  Richard
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons58898

Pörschke,  Klaus-Richard
Research Group Pörschke, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Cui, H., Goddard, R., & Pörschke, K.-R. (2012). Degradation of Dichloromethane by Bispidine. Journal of Physical Organic Chemistry, (25), 814-827. doi:10.1002/poc.2909.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000E-F20D-1
Abstract
An effective degradation reaction of CH2Cl2 by bispidine (3,7-diazabicyclo[3.3.1]nonane, C7H12(NH)2, 1) is reported. The reaction starts as low as -20?degrees C and is quantitative with respect to 1. The overall reaction implies nucleophilic substitution of chloride, followed by a series of cascading acidbase reactions, ending with the formation of two easily separable products, one being soluble and the other insoluble. The starting 1, the intermediates, and the products show a variety of interesting solid-state structures, associated with plasticity, NH?N and NH?Cl?HN hydrogen bonding, and polymorphism. Copyright (c) 2012 John Wiley & Sons, Ltd.