Abstract
An x-ray structural investigation of the products of the reactions of 1,3-di(tert-butyl)-2,4-di(tert-butylamido)diazadiphosphetidine and 1,3-dicyclohexyl-2,4-di(cyclohexylamido)diazadiphosphetidine with carbon disulfide and benzaldehyde, respectively, has been carried out (λMo, 2006 and 1484 reflections, R=0.038 and 0.083). It has been shown that in the former reaction the four-membered P2N2 ring is maintained, and a new exocyclic bond appears between one of its P atoms and the carbon atom of carbon disulfide with the formation of a zwitterionic adduct with the formula C15H38N4P2·CS2. In the latter case the P2N2 ring is opened, and a new five-membered heterocycle is closed with the formation of 2,5-diphenyl-3-cyclohexyl-4-oxo-4-cyclohexylamido-1,3,4-oxazaphospholidine C26H35O2N2P. The geometric parameters of both molecules investigated have been analyzed in detail.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
Sh. Égamberdiev, M. M. Yusupov, N. K. Rozhkova, et al., Uzb. Khim. Zh., No. 6, 31–36 (1981).
M. M. Yusupov, Sh. Égamberdiev, M. K. Makhmudov, and B. Tashkhodzhaev, Zh. Obshch. Khim.,54, 2705–2707 (1984).
V. A. Frenz, in: H. Schenk, R. Olthof-Hazelkamp, H. van Konigsfeld, and G. C. Bassi (editors), Computing in Crystallography, Delft University Press, Delft, Holland (1976), p. 64.
V. I. Andrianov, Z. Sh. Safina, and B. L. Tarnopol'skii, Rentgen-75. Automated System of Programs for Interpreting the Structures of Crystals. Description and Instructions [in Russian], OIKhF Akad. Nauk SSSR, Chernogolovka (1975).
S. Samdal and H. M. Seip, Acta Chem. Scand.,25, 1903–1904 (1971).
A. Almenningen, L. Fernholt, H. M. Seip, et al., Acta Chem. Scand.,A28, 1037–1041 (1974).
H. W. Kroto and B. M. Landsberg, J. Mol. Spectrosc.,62, 346–348 (1976).
J. Rooij, F. C. Mijhoff, and G. Renes, J. Mol. Struct.,25, 169–171 (1975).
N. G. Bokii, Yu. T. Struchkov, A. E. Kalinin, et al., Itogi Nauki Tekh., Ser. Kristallokhim. (1983).
V. A. Naumov and L. V. Vilkov, Molecular Structures of Organophosphorus Compounds [in Russian], Nauka, Moscow (1986).
L. Pauling, The Nature of the Chemical Bond, 3rd edn., Cornell Univ. Press, Ithaca (1960), p. 224.
S. Kleemann, E. Fluck, and W. Schwarz, Phosphorus Sulfur,12, 19–25 (1981).
S. Fox, Z. Naturforsch, b33, 610–612.
E. Fluck, H. Richter, H. Riffel, and H. Hess, Phosphorus Sulfur,14, 87–91 (1982).
C. Romming and J. Songstad, Acta Chem. Scand.,A34, 631–637 (1980).
A. Aaberg, T. Gramstad, and S. Husebye, Acta Chem. Scand.,A34, 717–724 (1980).
A. N. Chernega, M. Yu. Antipin, Yu. T. Struchkov, et al., Zh. Strukt. Khim.,28, No. 2, 135–139 (1987).
A. N. Chernega, M. Yu. Antipin, Yu. T. Struchkov, et al., Zh. Strukt. Khim.,29, No. 2, 143–148 (1988).
W. Schwarz, H. Hess, and W. Zeiss, Z. Naturforsch.,b33, 723–726 (1978).
H. R. Allcock, Phosphorus-Nitrogen Compounds: Cyclic, Linear, and High-polymeric Systems, Academic Press, New York (1972) [Russian translation: Mir, Moscow (1976)].
E. Flock, H. Riffel, and H. Richter, Phosph. Sulfur,24, 273–276 (1985).
G. Baccolini and A. Krajewski, J. Chem. Soc., Perkin Trans.1, 893–898 (1979).
Additional information
Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. A. N. Nesmeyanov Institute of Organometallic Compounds, Academy of Sciences of the USSR. Institute of Organic Chemistry, Academy of Sciences of the Ukrainian SSR. Translated from Zhurnal Strukturnoi Khimii, Vol. 32, No. 2, pp. 133–138, March–April, 1991.
Rights and permissions
About this article
Cite this article
Tashkhodzhaev, B., Chernega, A.N., Yanovskii, A.I. et al. X-ray structural investigation of the adduct of 1,3-di(tert-butyl)-2,4-di(tert-butylamido)diazadiphosphetidine with carbon disulfide and 2,5-diphenyl-3-cyclohexyl-4-oxo-4-cyclohexylamido-1,3,4-oxazaphospholidine. J Struct Chem 32, 264–268 (1991). https://doi.org/10.1007/BF00777199
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00777199