Highly Regioselective C(3) Opening of an Aromatic 2,3‐Epoxy Alcohol with Sodium Phenoxides or Thiophenoxides (=Benzenethiolates) Supported by β‐Cyclodextrin in Water |
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| Authors: | Mendu Narender Majjigapu Somi Reddy Yadavalli Venkata Durga Nageswar Kakulapati Rama Rao |
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| Affiliation: | 1. Organic Chemistry Division‐I, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad‐500?007, India, (phone: +91?40?27193164;2. fax: +91?40?27160757) |
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| Abstract: | 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). |
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| Keywords: | Alcohol, 2,3‐epoxy Phenoxide, sodium salt Thiophenoxide Benzenethiolates Propane‐1,2‐diol Cyclodextrins Ring‐opening reaction |
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