Jump to ContentJump to Main Navigation
Show Summary Details
More options …

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

Online
ISSN
1865-7117
See all formats and pricing
More options …
Volume 33, Issue 10

Issues

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

Abstract

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.

Export Citation

© 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

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Christian Depken, Felix Krätzschmar, Rene Rieger, Katharina Rode, and Alexander Breder
Angewandte Chemie International Edition, 2018, Volume 57, Number 9, Page 2459
[2]
Christian Depken, Felix Krätzschmar, Rene Rieger, Katharina Rode, and Alexander Breder
Angewandte Chemie, 2018, Volume 130, Number 9, Page 2484

Comments (0)

Please log in or register to comment.
Log in