Highly Regioselective C(3) Opening of an Aromatic 2,3-Epoxy Alcohol with Sodium Phenoxides or Thiophenoxides (=Benzenethiolates) Supported by β-Cyclodextrin in Water

A simple and mild procedure was developed for the first time for the C(3)‐selective ring opening of an aromatic 2,3‐epoxy alcohol, i.e., of trans‐3‐phenyloxirane‐2‐methanol (1), with sodium phenoxides or thiophenoxides (=benzenethiolates) 2 supported by β‐cyclodextrin in H2O at 50° to afford the cor...

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Bibliographic Details
Published in:Helvetica chimica acta 2007-06, Vol.90 (6), p.1107-1111
Main Authors: Narender, Mendu, Reddy, Majjigapu Somi, Nageswar, Yadavalli Venkata Durga, Rao, Kakulapati Rama
Format: Article
Language:English
Subjects:
2-diol
3-epoxy
Alcohol
Alcohol, 2,3‐epoxy
Benzenethiolates
Cyclodextrins
Phenoxide
Phenoxide, sodium salt
Propane-1
Propane‐1,2‐diol
Ring-opening reaction
sodium salt
Thiophenoxide
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Summary:A simple and mild procedure was developed for the first time for the C(3)‐selective ring opening of an aromatic 2,3‐epoxy alcohol, i.e., of trans‐3‐phenyloxirane‐2‐methanol (1), with sodium phenoxides or thiophenoxides (=benzenethiolates) 2 supported by β‐cyclodextrin in H2O at 50° to afford the corresponding 3‐(aryloxy)‐ or 3‐(arylthio)propane1,2‐diols 3 in excellent yields (Scheme, Table).
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.200790109