Journal of Organic Chemistry p. 2473 - 2476 (1981)
Update date:2022-07-29
Topics:
Nolan, Steven M.
Cohen, Theodore
Treatment of 2-alkylfurans with butyllithium followed by diphenyl disulfide yields 2-(phenylthio)-5-alkylfurans.When the 2-(phenylthio)-3-bromo-5-alkylfurans arising by bromination of the latter are treated with tert-butyllithium, the corresponding 3-lithio derivative is produced and it can be trapped by electrophiles such as alkyl iodides, aldehydes, trimethylsilyl chloride, and carbon dioxide.Raney nickel desulfurization of the product of such trapping produces 4-substituted-2-alkylfurans.
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