Science of Synthesis

Zwanenburg, B., Science of Synthesis, (2004) 27, 138.

The reaction of α-silyl carbanions with sulfur dioxide constitutes a general method for the synthesis of a variety of sulfines.[‌23‌–‌28‌] This method is in fact a modification of the Peterson alkenation reaction. The required α-silyl carbanions are conveniently obtained from appropriate active methylene compounds by deprotonation with, for example, butyllithium, followed by silylation using chlorotrimethylsilane, and subsequent deprotonation of the thus obtained silylated compound ‌10‌ with butyllithium. The thus produced silyl carbanion is then treated with an excess of sulfur dioxide.[‌23‌,‌24‌] It is assumed that initially an α-silyl sulfinate ‌11‌ is formed which smoothly eliminates trimethylsilanolate to produce the sulfine ‌7‌ (‌Scheme 7‌). This sequence can be conducted in a one-pot operation. A variety of active methylene compounds can be used as starting material; a typical selection is shown in ‌Scheme 7‌. The main limitation of this sulfine synthesis is that methylene compounds activated by carbonyl groups cannot be used due to deviating reactions of the enolate in the silylation step (O- instead of C-silylation).[‌6‌,‌17‌–‌19‌]

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		88 (88)	[‌88‌]

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References

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• 8.Meeeee-Meee, (8888) M 88-8, 888.