Nucleophilic Reactivity of Ethers Against Terminal Epoxides in the Presence of BF 3 : A Mechanistic Study | Zendy

Kose Aytekin | Zendy; Altundas Ramazan | Zendy; Seçen Hasan | Zendy; Kara Yunus | Zendy

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Nucleophilic Reactivity of Ethers Against Terminal Epoxides in the Presence of BF 3 : A Mechanistic Study

Author(s) -

Kose Aytekin,

Altundas Ramazan,

Seçen Hasan,

Kara Yunus

Publication year - 2013

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.201200438

Subject(s) - chemistry , epichlorohydrin , alkoxy group , nucleophile , reactivity (psychology) , cleavage (geology) , ring (chemistry) , epoxide , medicinal chemistry , stereochemistry , organic chemistry , alkyl , catalysis , medicine , alternative medicine , geotechnical engineering , pathology , fracture (geology) , engineering

In the presence of BF 3 , a series of symmetrical and unsymmetrical ethers reacted with epichlorohydrin and 2‐[(benzyloxy)methyl]oxirane, two terminal epoxides, to afford 1‐alkoxy‐3‐chloropropan‐2‐ol and 1‐alkoxy‐3‐(benzyloxy)propan‐2‐ol. The cleavage of unsymmetrical ethers occurred via an S N 2 or S N 1 mechanism. Secondary epoxides did not give similar ring‐opening products.

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