78571-75-2Relevant academic research and scientific papers
Using N-nitrosodichloroacetamides to conveniently convert linear primary amines into alcohols
Macarthur, Nicholas S.,Wang, Linshu,Mccarthy, Blaine G.,Jakobsche, Charles E.
supporting information, p. 2014 - 2021 (2015/08/18)
The reported rearrangement of N-nitrosodichloroacetamides provides a practicalmethod for converting primary amines into primary alcohols. The reaction sequence is operationally simple, requires only a single purification, and is compatible with a number of common functional groups. Mechanistic studies of the nitrosylation and rearrangement reactions illustrate the increased utility of dichloroacetamides compared to various other amides for this transformation.
Acid-Catalyzed Rearrangement of Propella-ε-lactones
Kakiuchi, Kiyomi,Tsugaru, Toshinori,Tobe, Yoshito,Odaira, Yoshinobu
, p. 4204 - 4208 (2007/10/02)
The acid-catalyzed rearrangement of - and propella-ε-lactones 9 and 10 in boiling acetic acid takes place readily to afford the 1,2-disubstituted cyclopentene 21 and cyclohexene 26 as the major products, respectively, while such lactone ring cleavage of the - and propella-δ-lactones 1 and 2 does not occur at all under similar conditions.The remarcable distinction in reactivity in the acid-catalyzed rearrangement between the ε-lactones and the δ-lactones is attributed to the effect of lactone ring size.
