405924-08-5Relevant articles and documents
Oxygenation of Simple Olefins through Selective Allylic C?C Bond Cleavage: A Direct Approach to Cinnamyl Aldehydes
Liu, Jianzhong,Wen, Xiaojin,Qin, Chong,Li, Xinyao,Luo, Xiao,Sun, Ao,Zhu, Bencong,Song, Song,Jiao, Ning
supporting information, p. 11940 - 11944 (2017/09/20)
A novel metal-free allylic C?C σ-bond cleavage of simple olefins to give valuable cinnamyl aldehydes is reported. 1,2-Aryl or alkyl migration through allylic C?C bond cleavage occurs in this transformation, which is assisted by an alkyl azide reagent. This method enables O-atom incorporation into simple unfunctionalized olefins to construct cinnamyl aldehydes. The reaction features simple hydrocarbon substrates, metal-free conditions, and high regio- and stereoselectivity.
Regiochemistry of Nucleophilic Opening of β-Substituted Styrene Oxides with Thiolate Anions: Model Experiments in the Synthesis of Leukotriene Analogues
Marples, Brian A.,Saint, Christopher G.,Traynor, John R.
, p. 567 - 574 (2007/10/02)
β-Substituted trans-styrene oxides are cleaved with thiolate anions highly regioselectively by attack at the α-carbon whereas the cis-isomers are cleaved by attack at the α- and β-carbons.Cysteine, in a suitably protected form, similarly cleaves β-substituted trans-styrene oxides, thus allowing the synthesis of a simple LTE model.
