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

Narender Mendu | Zendy; Reddy Majjigapu Somi | Zendy; Nageswar Yadavalli Venkata Durga | Zendy; Rao Kakulapati Rama | Zendy

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

Author(s) -

Narender Mendu,

Reddy Majjigapu Somi,

Nageswar Yadavalli Venkata Durga,

Rao Kakulapati Rama

Publication year - 2007

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200790109

Subject(s) - chemistry , regioselectivity , epoxy , methanol , alcohol , cyclodextrin , ring (chemistry) , sodium , medicinal chemistry , organic chemistry , catalysis

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 H 2 O at 50° to afford the corresponding 3‐(aryloxy)‐ or 3‐(arylthio)propane1,2‐diols 3 in excellent yields ( Scheme, Table ).

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