Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway
Yükleniyor...
Dosyalar
Tarih
2018
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Beilstein-Institut
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
The present work describes an unfamiliar reaction of 5-(chloromethyl)-3-substituted-phenyl-1,2,4-oxadiazoles with KCN affording trisubstituted 1,2,4-oxadiazol-5-ylacetonitriles and their parent alkanes, namely, 1,2,3-trisubstituted- 1,2,4-oxadiazol-5-ylpropanes. To the best of our knowledge, the current synthetic route leading to decyanated products will be the first in terms of a decyanation process which allows the transformation of trisubstituted acetonitriles into alkanes by the incorporation of KCN with the association of in situ-formed HCN and most likely through the extrusion of cyanogen which could not be detected or isolated. In addition, the plausible mechanisms were proposed for both transformations. The structures of the title compounds were identified by means of IR, H-1 NMR, C-13 NMR, 2D NMR spectra, TOF-MS and X-ray measurements.
Açıklama
Anahtar Kelimeler
Decyanation, KCN, 1,2,4-Oxadiazole
Kaynak
Beilstein Journal Of Organic Chemistry
WoS Q Değeri
Q2
Scopus Q Değeri
Q2
Cilt
14
