Iron-Promoted 1,5-Substitution (SN2′′) Reactions of Enyne Acetates and Oxiranes with Grignard Reagents
Asian Journal of Organic Chemistry, cilt.6, sa.10, ss.1415-1420, 2017 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 6 Sayı: 10
- Basım Tarihi: 2017
- Doi Numarası: 10.1002/ajoc.201700225
- Dergi Adı: Asian Journal of Organic Chemistry
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.1415-1420
- Anahtar Kelimeler: enynes, Grignard reaction, iron, nucleophilic substitution, regioselectivity
- Trakya Üniversitesi Adresli: Evet
Özet
Acetate derivatives of 2-en-4-yne alcohols 1 and enyne oxiranes 4 regioselectively underwent 1,5-substitution (SN2′′) reactions with Grignard reagents in the presence of an iron compound to provide vinylallenes exclusively with the (E)-configuration. An alkali salt was needed to avoid the hydride-promoted reductive 1,5-substitution pathway for 1, whereas no such additive was needed for the effective conversion of 4 into the desired alkylated or arylated vinylallene structure.