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Synthesis and Stereochemistry of Mono and Bicyclic 1,2-Thiaphosphacyclanes

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The facile synthetic route to 5- and 6-membered mono and bicyclic 3-cyano-2-oxo-1,2- thiaphosphacyclanes has been elaborated on the base of intramolecular S-alkylation in a series of mono- and bis-_-haloalkyl substituted thiophosphorylacetonitriles. The stereochemistry of the cyclic compounds was determined byNMRas well as X-ray diffraction. The diastereomeric transformations of 3-cyano-2-oxo-1,2-thiaphosphinanes and formation of conglomerates in the case of 6-cyano-2-oxa-10-thia-1-phosphabicyclo[4.4.0]decane- 1-oxide are discussed.
Rocznik
Strony
1103--1119
Opis fizyczny
Bibliogr. 37 poz., rys.
Twórcy
  • A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 117813 Moscow, GSP-1, Vavilova str.28, Russia
  • A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 117813 Moscow, GSP-1, Vavilova str.28, Russia
  • A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 117813 Moscow, GSP-1, Vavilova str.28, Russia
  • A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 117813 Moscow, GSP-1, Vavilova str.28, Russia
  • A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 117813 Moscow, GSP-1, Vavilova str.28, Russia
Bibliografia
  • 1.Quin L.D., The Heterocyclic Chemistry of Phosphorus Systems Based on the Phosphorus-Carbon Bond. Wiley-Interscience, 1981.
  • 2.Pudovik M.A., Cherkasov R.A., Ovchinnikov V.V. and Pudovik A.N., Usp. Khim., 51(8), 1305 (1982).
  • 3.Pudovik M.A., Ovchinnikov V.V. and Cherkasov R.A., ibid., 52(4), 640 (1983).
  • 4.Polezhaeva N.A. and Cherkasov R.A., ibid., 54(11), 1899 (1985).
  • 5.Polezhaeva N.A. and Cherkasov R.A., ibid., 56(2), 287 (1987).
  • 6.Mironov V.F., Pudovik M.A. and Sinyashin O.G., Zhurn. Rus. Khim. Obch., 69( 1), 13 (1999).
  • 7.Gamer A.Y., Pat.US 2916510; C. A., 54, 5571 (1960).
  • 8.Gamer A.Y., Pat.US 2953591; C. A., 55, 5347 (1961).
  • 9.Kleiner H., Finke M., Bollert U. and Herwig W., Pat. DE 2346787 (1975); C. A., 83, 44266 (1975).
  • 10.Matsumoto T., Kanatsuki O. and Hamada S., Jpn. Kokai Tokkyo Koho Yp 63280728; C. A., 111, 40152 (1989).
  • 11.Ueda A. and Matsumoto T., Jpn. Kokai Tokkyo Koho Yp 62185710; C. A., 108, 96114 (1988).
  • 12.Germanaud L., Brunei. S. Chevalier Y. and Le Perchec P., Bull. Soc. Chim. Fr., 699 (1988).
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  • 14.Mathey F. and Thavard D., J. Organomet. Chem., 117, 377 (1976).
  • 15.Arbuzov B.A., Nikonova L.Z. and Nuretdinova O.N., Izv. AN USSR, Ser. khim., 648 (1973).
  • 16.Uhing E.H., Pat US 4231970, C. A., 94, 84303 (1981).
  • 17.Uhing E.H., Pat US 4540526, C. A., 94, 84303 (1981).
  • 18.Aladzheva I.M., Bykhovskaya O.V., Lobanov D.I., Lyssenko K.A., Shishkin O.V., Antipin M.Yu., Struchkov Yu.T., Mastryukova T.A. and Kabachnik M.I., Mend. Commun., 58 (1996).
  • 19.Lobanov D.I., Aladzheva I.M., Bykhovskaya O.V., Petrovskii P.V., Lyssenko K.A., Antipin M.Yu., Mastryukova T.A. and Kabachnik M.I., Phosphorus, Sulfur and Silicon, 128, 145 (1997).
  • 20.Aladzheva I.M., Bykhovskaya O.V., Lobanov D.I., Petrovskii P.V., Lyssenko K.A., Antipin M.Yu., Mastryukova T.A. and Kabachnik M.I., Zhurn. Obsch. Khim., 68(9), 1421 (1998).
  • 21.Mastryukova T.A., Aladzheva I.M., Lobanov D.I., Bykhovskaya O.V., Petrovskii P.V., Lyssenko KA. and Kabachnik M.I., Phosphorus, Sulfur and Silicon, 144-146, 569 (1999).
  • 22.Odinets I.L., Vinogradova N.M., Artyushin O.I., Kalyanova R.M., Lyssenko K.A., Petrovskii P.V., Mastryukova T.A. and Kabachnik M.I., Izv. AN, Ser. khim., 990 (1998).
  • 23.Vinogradova N.M., Odinets I.L., Artyushin O.l., Lyssenko K.A., Petrovskii P.V. and Mastryukova T.A., Phosphorus, Sulfur and Silicon, 144-146, 589 (1999).
  • 24.Vinogradova N.M., Odinets I.L., Artyushin O.I., Petrovskii P.V., Lyssenko K.A., Antipin M.Yu. and Mastryukova T.A., Zhurn. Obsch. Khim., 68(9), 1434 (1998).
  • 25.Aksnes G. and Bergessen K., Acta Chem. Scand., 20, 2508 (1966).
  • 26.Wroblewski A.E., Tetrahedron, 39, 1809 (1983).
  • 27.Thompson C.M., Frick J.A. and Green D.L., J. Org. Chem., 55(1), 111 (1990).
  • 28.Odinets I.L., Vinogradova N.M., Artyushin O.I., Petrovskii P.V., Lyssenko K.A., Antipin M.Yu. and Mastryukova T.A., Mendeleev Commun., 158 (1999).
  • 29.Desiaiju G.R., Acc. Chem. Res., 29, 441, 1996.
  • 30.Vinogradova N.M., Lyssenko K.A., Odinets I.L., Petrovskii P.V., Mastryukova T.A. and Kabachnik M.I., Phosphorus, Sulfur and Silicon, 132, 265 (1998).
  • 31.Odinets I.L., Vinogradova N.M., Lyssenko K.A., Petrovskii P.V. and Mastryukova T.A., Heteroatom Chem., 11, 163 (2000).
  • 32.Bellard S., Postle S. and Sheldrick G.M., Acta Cryst. B, 34, 1032 (1978).
  • 33.Cremer S.E., Sommese A.G. and Rodriques O., Phosphorus, Sulfur and Silicon, 75, 107 (1993).
  • 34.Lane T., Rodriques O.P., Tasz M.K., Sommese A.G. and Cremer S.E., Phosphorus, Sulfur and Silicon, 102, 115(1995).
  • 35.Lane T., Rodriques O.P. and Cremer S.E., Phosphorus, Sulfur and Silicon, 103, 63 (1998).
  • 36.Polosov A.M. and Cremer S.E., Phosphorus, Sulfur and Silicon, 147, 335 (1998).
  • 37.Jacques J., Collet A. and Wilen S.M., Enantiomere, Racemates, and Resolutions. Krieger Publ. Comp., Malabar, Florida, 1994.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0019-0021
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