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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences


IMPACT FACTOR 2018: 0.961

CiteScore 2018: 0.91

SCImago Journal Rank (SJR) 2018: 0.263
Source Normalized Impact per Paper (SNIP) 2018: 0.505

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1865-7117
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Volume 34, Issue 1

Issues

Reactions of t-Butyl Peresters, XVIII Peroxyester Reaction of t-Butyl N,N-Dimethylperoxyamidate

David J. Rawlinson / Maria Konieczny / George Sosnovsky
Published Online: 2014-06-02 | DOI: https://doi.org/10.1515/znb-1979-0116

Abstract

The thermal copper ion catalyzed peroxyester reaction of t-butyl N,N-dimethylperoxyamidate (1, R = N(CH3)2) with cyclohexene results in the formation of the corresponding N,N-dimethylamidate 6 in 20% yield, and 3,3′-dicyclohexenyl (5) in 40% yield. Under

analogous conditions, the reaction of 1, R = N(CH3)2, with tetrahydrofuran gives the corresponding amidate 7 in 6% yield. Only a 2% yield of 6 and no 7 were isolated in the

photochemical variant of the peroxyester reaction. Compound 6 is also obtained in a 12% yield from the reaction of 2-cyclohexen-1-ol (9) with N,N-dimethyl carbamoyl chloride (4) in the presence of pyridine.

Keywords: Copper Ion Catalysis; Photochemistry of Perester; t-Butyl N,N-Dimethylperoxyamidate; N,N-Dimethylamidates; 2-Cyclohexen-1 -ol

About the article

Received: 1978-07-17

Published Online: 2014-06-02

Published in Print: 1979-01-01


Citation Information: Zeitschrift für Naturforschung B, Volume 34, Issue 1, Pages 76–80, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-1979-0116.

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© 1946 – 2014: Verlag der Zeitschrift für Naturforschung. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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[1]
D. J. RAWLINSON, M. KONIECZNY, and G. SOSNOVSKY
Chemischer Informationsdienst, 1979, Volume 10, Number 15

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