Synthesis of β-Trimethylsilyloxythioethers and β-Hydroxythioethers by the Reaction of Epoxides with Aryl- and Alkylthiotrimethylsilanes

References

• Murphy , R. C. , Hammarström , S. and Samuelsson , B. 1979 . Proc. Natl. Acad. Sci. U.S.A. , 76 : 4275
   PubMed Web of Science ®Google Scholar
• Parker , C. W. , Huber , M. M. , Hoffman , M. K. and Falkenhein , S. F. 1979 . Prostaglandins , 18 : 673
   PubMed Web of Science ®Google Scholar
• Morris , H. , Taylor , G. W. , Piper , P. , Samhoun , M. N. and Tippins , J. R. 1980 . Prostaglandins , 19 : 185
   PubMed Web of Science ®Google Scholar
• Rokach , J. , Girard , Y. , Guindon , Y. , Atkinson , J. G. , Larue , M. , Young , R. N. , Masson , P. and Holme , G. 1980 . Tetrahedron Lett. , 21 : 1485
   Web of Science ®Google Scholar
• Abel , E. W. and Walker , D. J. 1968 . J. Chem. Soc., A , : 2338
   Web of Science ®Google Scholar
• Hanessian , S. and Guindon , Y. 1980 . Tetrahedron Lett. , 21 : 2305
   Web of Science ®Google Scholar
• Takeuchi , Y. , Demachi , Y. and Yoshii , E. 1979 . Tetrahedron Lett. , 20 : 1231
   Google Scholar
• Hanessian , S. and Guindon , Y. 1980 . Carbohydr. Res. , accepted for publication
   Google Scholar
• Trost , B. M. , Ochiai , M. and McDougal , P. G. 1978 . J. Am. Chem. Soc. , 100 : 7103
   Web of Science ®Google Scholar
• The partial formation of the 1,4-adducts could indicate that the reaction proceeds through a discrete allylic cation in these cases. However, we feel that these products arise through an SN 2' type mechanism based on the fact that in none of the cases studied (e.g. entries 3. and 5. - Table I) have we observed any products of SN1. type attack. The possibility that the 1,4-adducts could arize from a rearrangement of the initially formed 1,2-adducts, would seem to be ruled out based on the observation that these products are stable to the reaction conditions
   Google Scholar
• The classical conditions for opening activated epoxides, RSH, Et3N (see The Chemistry of the Thiol Group, Part 2, Chapter 16, Ed. by S. Patai, John Wiley & Sons, 1974) when applied to the reaction of thiophenol and butadiene mono-oxide gave a 3:2. mixture of 1,2- and 2,1-hydroxythioethers. These conditions, when applied to less activated epoxides either gave no reaction or at best very slow reactions
   Google Scholar
• Glass , R. S. 1973 . J. Organomet. Chem. , 61 : 83
   Web of Science ®Google Scholar
• Ojima , I. , Nihonyanagi , M. and Nagai , Y. 1973 . J. Organomet. Chem. , 50 : C-26
   Web of Science ®Google Scholar
• Detty , M. R. and Wood , G. P. 1980 . J. Org. Chem. , 45 : 80
   Web of Science ®Google Scholar
• Kita , Y. , Haruta , J. , Segawa , J. and Tamura , Y. 1979 . Tetrahedron Lett. , 20 : 4311
   Google Scholar