Dithiophosphorylation of cyclic monoterpenes

Article abstract of DOI:10.1080/10426500701796470

New data are presented for the synthesizing terpene esters of dithiophosphoric acids and their structure. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/10426500701796470

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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Dithiophosphorylation of Cyclic
Monoterpenes
Il'yas S. Nizamov a b , Artiem V. Sofronov a , Rafael
A. Cherkasov a & Liliya E. Nikitina c
a Kazan State University , Kazan, Russia
b A. E. Arbuzov Institute of Organic and Physical
Chemistry , Kazan, Russia
c Kazan State Medical University, Butlerov , Kazan,
Russia
Published online: 20 Jun 2008.
To cite this article: Il'yas S. Nizamov , Artiem V. Sofronov , Rafael A. Cherkasov
& Liliya E. Nikitina (2008) Dithiophosphorylation of Cyclic Monoterpenes,
Phosphorus, Sulfur, and Silicon and the Related Elements, 183:2-3, 675-676, DOI:
10.1080/10426500701796470
To link to this article: http://dx.doi.org/10.1080/10426500701796470
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Phosphorus, Sulfur, and Silicon, 183:675–676, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500701796470
Dithiophosphorylation of Cyclic Monoterpenes
Il’yas S. Nizamov,1,2 Artiem V. Sofronov,1
Rafael A. Cherkasov,1 and Liliya E. Nikitina3
1Kazan State University, Kazan, Russia
2A. E. Arbuzov Institute of Organic and Physical Chemistry,
Kazan, Russia
3Kazan State Medical University, Butlerov Kazan, Russia
New data are presented for the synthesizing terpene esters of dithiophosphoric acids
and their structure.
Keywords Cyclic monoterpenes; Lewis acid cataysts; thiophosphorylation
We have carried out the reactions of dithiophosphoric acids with such
terpenes as racemic camphene, (+)-limonene, (1S)-(−)-β-pinene and 3-
carene under mild conditions. These reactions occur at 20◦C for 1–3 h in
Address correspondence to Il’yas S. Nizamov Kazan State University, Kremlievskaya
Str., 18, Kazan, 420008, Russia. E-mail:ilyas.nizamov@ksu.ru
675

676
I. S. Nizamov et al.
the presence of catalytic amounts of anhydrous ZnCl2 to yield adducts
formed in accordance with Markovnikow’s rule. In the case of camphene
the adduct formation is accompanied by skeleton transformation into
norbornane structure. The reactions O,O-dialkyl dithiophosphoric acids
with (+)-limonene proceed with the participation of the exocyclic C=C
bond.
The reactions studied are facilitated by Lewis acid cataysts (NiCl2,
CuCl, CuCl2, FeCl3, BF.3Et2O, AlCl3). The reactions of O,O-dialkyl
dithiophosphoric acids with (1S)-(-)-β-pinene can also be performed
non-catalytically.
REFERENCES
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Abstr., 43, 2930a (1953).
[2] F. B. Augustine, U.S. Patent 2665295 (1954); Chem. Abstr., 48, 12,807f (1954).