Nucleophilic Reactivity of Ethers Against Terminal Epoxides in the Presence of BF3 : A Mechanistic Study

Kose A., Altundas R., SEÇEN H., KARA Y.

HELVETICA CHIMICA ACTA, cilt.96, sa.7, ss.1325-1330, 2013 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 96 Sayı: 7
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1002/hlca.201200438
  • Dergi Adı: HELVETICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1325-1330
  • Anahtar Kelimeler: Epoxides, terminal, Nucleophilic reactivity, Ether cleavage, Alkoxonium ions, Boron trifluoride
  • Atatürk Üniversitesi Adresli: Evet

Özet

In the presence of BF3, 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.