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8.1.20.2 Method 2: Alkylation of α-Lithio Sulfoxides

DOI: 10.1055/sos-SD-008-00403

Durst, T.; Khodaei, M.Science of Synthesis, (20068666.

Alkylation of the α-chloro-α-lithio sulfoxide 20 with a variety of primary bromoalkanes is quite efficient if carried out in the presence of 1 equivalent of hexamethylphosphoric triamide. This yields the chain-extended α-chloro sulfoxides 21. Thermolysis of these compounds in the presence of hydroquinone gives 1-chloroalkenes 22 in excellent yields (Scheme 9).[‌27‌] 1-Fluoroalkenes are formed commencing with the fluoro analogue of 20.[‌28‌]

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