期刊
CHEMISTRY LETTERS
卷 51, 期 2, 页码 170-172出版社
CHEMICAL SOC JAPAN
DOI: 10.1246/cl.210702
关键词
Heteroatom exchange; Oxazoline-enols; Dithiooxophosphorane analogues
资金
- Booster Fund (Ryerson University)
- Ad Hoc Research Fund (Ryerson University)
- Ontario Graduate Scholarship
- Faculty of Science Molecular Science Award
- Ryerson Graduate Student Fellowship
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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