Synthesis of a Cyclic 3-Methylsulfonyl Enol Ether

Dedicated to Professor Hans-Ulrich Reissig on the occasion of his 66^th birthday

Abstract

Electrophilic introduction of a methylmercapto group into dihydropyran gives 3-methylmercaptodihydropyran, which is readily oxidized to 3-methylsulfonyldihydropyran.

Key words

enol ether - methylmercapto - methylsulfonyl - methylsulfinyl - oxidation - Oxone

• References

• 1 Present address: Institut Für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany.
• 2 Skuballa W, Raduechel B, Vorbrueggen H. Tetrahedron Lett. 1988; 29: 4285
• 3 Meerwein H, Zenner KF, Gipp R. Liebigs Ann. Chem. 1965; 688: 67
• 4 Baldwin MJ, Brown RK. Can. J. Chem. 1967; 45: 1195
• 5 Brintzinger H, Pfannstiehl K, Koddebusch H. Chem. Ber. 1950; 83: 87
• 6 Freeman F, Angeletakis CN. J. Am. Chem. Soc. 1983; 105: 4039
• 7 de Lucchi O, Miotti U, Modena G. Org. React. 1991; 40: 157
• 8 Opitz O, Rieth KG, Walz G. Tetrahedron Lett. 1966; 5269
• 9 Opitz O, Bluecher D. Tetrahedron Lett. 1966; 5263
• 10 Beagley B, James M, Pritchard RG, Raynor CM, Smith C, Stoodley RJ. J. Chem. Soc., Perkin Trans. 1 1992; 2371
• 11 Skuballa W, Vorbrueggen H. Angew. Chem., Int. Ed. Engl. 1981; 20: 1046
• 12 Skuballa W, Schillinger E, Stuerzebecher CSt, Vorbrueggen H. J. Med. Chem. 1986; 29: 313