References
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- 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
- 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
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- Ojima , I. , Nihonyanagi , M. and Nagai , Y. 1973 . J. Organomet. Chem. , 50 : C-26
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- Kita , Y. , Haruta , J. , Segawa , J. and Tamura , Y. 1979 . Tetrahedron Lett. , 20 : 4311