Sulphur-mediated five-membered ring expansions. Steroidal examples

Paryzek, Z.; Martynow, Jacek

doi:10.1039/p19900000599

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Cited by 6 publications

(1 citation statement)

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“…Sulfur‐mediated semipinacol rearrangements are quite rare and have been reported mainly for ring expansion reactions of dithioacetals . Some rearrangements involving aromatic vinyl sulfides have been devised, and a singular case of a five‐membered ring expansion involving an alkyl vinyl sulfide has been reported . Under Brønsted acid catalysis, protonation of the thioenol ether in 3 may lead to the formation of an intermediate thiacarbenium ion A (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and olfactory evaluation of allylic α‐quaternary thioether ketones

Lempenauer

Appleson

Lemière

et al. 2018

Flavour & Fragrance J

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Novel α‐quaternary allylic thioether ketones were efficiently prepared from readily available α,β‐unsaturated ketones in an easily scalable two‐step procedure, with an acid‐catalysed skeletal rearrangement of 2‐(vinylthio) allylic alcohols as the key step. The sensory properties of this novel class of sulfur odorants were evaluated and all displayed green herbal and vegetal notes. An unexpected and interesting fresh patchouli note was observed for an alcohol derivative.

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Section: Resultsmentioning

confidence: 99%