Hydroxyalkylation of Lithiated Bis methylthio methane with Epoxides

4 Hydroxyalkylation of Lithiated Bis(methylthio)methane with Epoxides 

Epoxypropane (50% excess) and epoxystyrene (10% excess) are added between 

Epoxycyclohexane (20% excess) is added in one portion at — 20 °C, after which the temperature is allowed to rise (without cooling bath) to 15 °C. Above 0°C the heating effect is easily observable. After an additional 45 min (at 15 to 20 °C) the product (b.p. 120°C/0.5 mmHg, nD(20) 1.5519, yield 90%) is isolated as described above. 

The 1H- and 13C-NMR spectra of the products obtained from propylene oxide, styrene oxide, and cyclohexene oxide show two CH3S-signals. 

Seebach D, Corey EJ (1975) J Org Chem 40 231. The reactions with epoxides are described as being very slow and reaction times prescribed for /Miydroxy alkylations are of the order of 1 week at — 5 or 

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