Journal
CHEMISTRY LETTERS
Volume 51, Issue 2, Pages 170-172Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/cl.210702
Keywords
Heteroatom exchange; Oxazoline-enols; Dithiooxophosphorane analogues
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Funding
- Booster Fund (Ryerson University)
- Ad Hoc Research Fund (Ryerson University)
- Ontario Graduate Scholarship
- Faculty of Science Molecular Science Award
- Ryerson Graduate Student Fellowship
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This article describes the exploration of S or Se and O exchange with (Z)-1-R-2-(4',4'-dimethyl-2'-oxazolin-2'-yl)-eth-1-en-1-ols. Rare analogues of thioester or selenoesters were isolated using P4S10 or Lawesson's Reagent.
The exploration of S- or Se-for-O exchange with (Z)-1-R-2-(4',4'-dimethyl-2'-oxazolin-2'-yl)-eth-1-en-1-ols (1: R = Ph, Me, CF3, Ph-p-OMe) is described. The use of P4S10, intended to facilitate O <-> S exchange, leads to the isolation of rare examples of air-stable thioester analogues of dithiooxophosphoranes. Clean heteroatom exchange can be realized using Lawesson's Reagent in good to moderate yields. Woollins' selenation reagent leads to the isolation of an unusual example of a selenazolidine product (10) in trace amounts.
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