TY  - JOUR
A1  - Bock, Hans
A1  - Dammel, Ralph
T1  - Gasphasen-Reaktionen, 58 [1, 2]. β-Chlorethylazid: HCl-Eliminierung und Pyrolyse
T1  - Gas phase reactions, 58 [1, 2]. β-chloroethyl ezide: HCl elimination and pyrolysis
T2  - Zeitschrift für Naturforschung, B
N2  - The HCl elimination from β-chloroethyl azide (1-azido-2-chloroethane) over potassium tert. butanolate at 350 K in a low pressure flow system is optimized using PE spectroscopic real-time gas analysis. The highly explosive vinyl azide formed can be purified by cool-trapping the by-products. Its subsequent and virtually hazard-free pyrolysis yields 2H-azirine, which can be isolated at temperatures below 240 K.
In contrast, the direct pyrolysis of β-chloroethyl azide requires temperatures above 710 K and results in a simultaneous split-off of both HCl and N2, yielding acetonitrile as the main thermolysis product. No intermediates such as β-chloroethanimine or ketenimine are observed, a result which is interpreted in terms of chemical activation.
KW  - β-Chloroethyl Azide
KW  - Vinyl Azide
KW  - Ketene Imine
KW  - 2H-Azirine
KW  - Gas Phase Dehydrochlorination
Y1  - 2014
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/79975
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-799755
SN  - 1865-7117
SN  - 0932-0776
VL  - 42.1987
IS  - 3
SP  - 301
EP  - 307
PB  - Verlag der Zeitschrift für Naturforschung
CY  - Tübingen
ER  -