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Unexpected remarkable stability of primary ozonides derived from alkenyl stannanes. One-pot synthesis of 1,2-diols from alkynes.

Organic letters (2002-02-01)
Ana M Gómez, María D Company, Serafín Valverde, J Cristóbal López
RÉSUMÉ

Primary ozonides derived from alkenyl stannanes display an unusual stability and can be transformed into 1,2-diols by treatment with dimethyl sulfide and borane-methyl sulfide complex. This observation has been incorporated into the development of a novel one-pot strategy for the conversion of alkynes into 1,2-diols.

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Sigma-Aldrich
Borane dimethyl sulfide complex solution, 2.0 M in THF