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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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Volume 33, Issue 10


Reactions of t-Butyl Peresters, XVII The Photochemical Reaction of Dialkyl t-Butylperoxy Phosphates and Alkyl f-Butylperoxy Alkylphosphonates with Cyclohexene and Cyclopentene in the Presence of Copper Ions

George Sosnovsky / Gary Karas
Published Online: 2014-06-02 | DOI: https://doi.org/10.1515/znb-1978-1024


The photochemical reaction of dialkyl t-butylperoxy phosphates (1) and alkyl t-butylperoxy alkylphosphonates (2) with cyclohexene in benzene in the presence

of a catalytic amount of copper (I) bromide produced the corresponding phosphates (3) and phosphonates (4) in 50-70% yield. The analogous reaction of 1

(R = i-C3H7) with cyclopentene gave a 36% yield of cyclopent-l-en-3-yl di-isopropyl phosphate (5), which could not be obtained by the thermal copper ion catalyzed reaction. Benzene, benzophenone, and acetone were effective as triplet photosensitizers in the phosphorylation reaction. Typical free radical inhibitors, such as, galvinoxyl (6), 4-hydroxy- 2,2,6,6-tetramethylpiperidine-l-oxyl (7), and DPPH (8) retarded the photosensitized reaction. The reaction was not affected by the singlet sensitizer Eosin-Y.

: t-Butylperoxy Phosphates; t-Butylperoxy Phosphonates; Copper Ion Catalysis; Triplet Sensitizers; Photochemistry

About the article

Received: 1978-06-20

Published Online: 2014-06-02

Published in Print: 1978-10-01

Citation Information: Zeitschrift für Naturforschung B, Volume 33, Issue 10, Pages 1177–1183, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-1978-1024.

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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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