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Alkylation of 2-Lithio-1,3-dithianes with Arenesulfonates of Primary Alcohols

Dieter Seebach*, Eva-Maria Wilka

*Laboratory of Organic Chemistry, Wolfgang-Paulistrasse 10, HCI H331, 8093 Zuerich, Switzerland, Email:

D. Seebach, E.-M. Wilka, Synlett, 1976, 476-477.

DOI: 10.1055/s-1976-24092


Benzenesulfonates of primary alcohols react smoothly with lithio derivatives of 1,3-dithiane and 2-phenyl-1,3-dithiane at room temperature to give 2-alkyl derivatives in high yields.

see article for more examples


Tosylates give lower yields due to competing deprotonation of the methyl group.

Dieter Seebach, October 25, 2007

Key Words

1,3-Dithianes, Corey-Seebach Reaction

ID: J66-Y1976-070