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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 3
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Original Articles

The First Synthesis of (+)-(S,S)-1,1-Bis(p-Tolyl-Sulfinyl)Ethene, A Latent Chiral Ketene Equivalent in Diels-Alder Reaction

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Pages 233-244 | Published online: 19 Dec 2006

References

  • Rao , Y. K. and Nagarajan , M. 1984 . Synthesis , : 757
  • Paquette , L. A. , Moerck , R. E. , Harirchian , B. and Magnus , P. D. 1978 . J. Am. Chem. Soc., , 100 : 1597
  • Maignan , C . 1983 . Tetrahedron , 39 : 3245
  • Koizumi , T. , Hakamada , I and Yoshii , E. 1984 . Tetrahedron Lett. , 25 : 87
  • Maignan , C. , Guessous , A. and Rouessac , F . 1984 . Ibid. , 25 : 1727
  • Farina , G. , Montanari , F. and Negrini , A. 1959 . Gazz. Chim. Ital. , 89 : 1548
  • Mikolajczyk , M. , Midura , W. , Grzejszczak , S. and Zatorski , A. 1978 . J. Org. Chem. , 43 : 473 For the wittig-Horner reaction of dialkylphosphoryl sulfoxide with carbonyl compounds
  • Diethyl p- tolylthiomethanephosphonate (3) was obtained by Michael-Arbuzov reaction with chloromethyl p-tolylsulfide and triethyl phosphite in 91 % yield Bp. 139-143[ddot]C/0.23 torr
  • Stirling , C. J. M. 1963 . J. Chem. Soc. , : 5741
  • Hopkins , P. , Fuchs , P. L. and Mathiaparanam , P. 1972 . Ibid. , 37 : 1367 For chlorosulfenylation-dehydrochlorination reaction
  • Koizumi , T. , Hirai , H. and Yoshii , E. 1982 . J. Org. Chem. , 47 : 4004 references cited therein.
  • 2 A variety of oxidants (m-chloroperbenzoic acid, CrO3/AcOH, NaIO4/MeOH, H2O2) were employed for the oxidation of The use of mcpba was most efficient for increasing the yield ofd-.
  • The asymmetric induction observed in the Diels-Alder reaction of (+)-p-tolyl vinyl sulfoxide with cyclopentadiene was reported (lit. 3.) to be rather inefficient. Maignan et a. pointed out3a that more reactive ethylenic sulfoxides are required for the predominant formation of the endo cycloadduct. In our case only two cycloadducts are formed because of a C2 axis of symmetry of the starting d-bis-sulfoxide 1. The reaction between meso-. and cyclopentadiene also proceeded smoothly to give two diastereomeric cycloadducts in 97% yield.
  • Paquette , L. A. , Doecke , C. W. , Kearney , F. R. , Drake , A. F. and Mason , S. F. 1980 . J. Am. Chem. Soc. , : 102 7228
  • Richman , J. , Herrmann , J. L. , Schlessinger , R. H. , Yamashita , M. and Suzuki , M. Ibid. , 197 3653 One step conversion of bis-sulfoxide into the corresponding ketone have not been previously reported.
  • Janusz , J. M. , Gardiner , L. J. and Berson , J. A. 1977 . J. Amer. Chem. Soc. , 99 : 8509
  • The silylated dienes such as Danishefsky's diene reacted with this dienophile.
  • The addition of Lewis acid such as ZnCl2 changed the ratio of the diastereomers. The mechanistic explanation and the optimization of the diastereoselection by the use of various Lewis acids will be discussed elsewhere in a near future.
  • Freeman , P. K. , Balls , D. M. and Brown , D. J. 1968 . J. Org. Chem. , 33 : 2211

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