Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Transformation of Methylene Acetals to Bromoformates with a Combination of Trimethyl(phenylthio)silane and N-Bromosuccinimide

Transformation of Methylene Acetals to Bromoformates with a Combination of Trimethyl(phenylthio)silane and N-Bromosuccinimide
Yasuyoshi Miki, Shun Ohgami, Akira Nakamura, Misa Nogata, Yuuka Hirose, Hiromichi Fujioka, Tomohiro Maegawa
A novel transformation reaction of methylene acetals, using a combination of trimethyl(phenylthio)silane (PhSTMS) and N-bromosuccinimide (NBS) under mild reaction conditions, is described. Various methylene acetals were converted to their corresponding bromoformates in good to high yields. Under the given conditions, the reaction proceeded via a radical pathway. Further transformation of bromoformates to their corresponding epoxides was achieved by treatment with NaOMe.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00776

DOI: 10.1021/acs.joc.7b00776

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