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• W1986361478 abstract "Two (3,6-dihydro-2-methylsulfanyl-2H-thiapyran-2-yl)phosphonate derivatives have been chemoselectively oxidized on the thiopyran sulfur. The obtained allylic six-membered cyclic sulfoxides 2a and 2b were reacted under Pummerer reaction conditions leading to new thiopyran derivatives (4a and 6b, respectively). In both studied cases, the nucleophilic attack of β,γ-unsaturated thionium ion intermediate took place regioselectively at the γ-position (even when occupied by a methyl substituent like in 2b). An unexpected second product 7b was however obtained from substrate 2b (having the dimethyl-substituted double bond). Dephosphorylation of 7b under basic conditions led to an original conjugated tri-unsaturated trifluromethylcarbonyl thiopyran product (8b). These results represent new original examples of the Pummerer reaction." @default.
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• W1986361478 date "2008-07-01" @default.
• W1986361478 modified "2023-10-16" @default.
• W1986361478 title "Pummerer-type reactions in the (2-methylsulfanyl-2-phosphonyl) thiopyran 1-oxide series" @default.
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• W1986361478 doi "https://doi.org/10.1016/j.tetlet.2008.05.032" @default.
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