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

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 t...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2017-07, Vol.82 (14), p.7608-7613
Hauptverfasser: Maegawa, Tomohiro, Nogata, Misa, Hirose, Yuuka, Ohgami, Shun, Nakamura, Akira, Miki, Yasuyoshi, Fujioka, Hiromichi
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00776