55941-61-2Relevant academic research and scientific papers
Practical β-masked formylation and acetylation of electron-deficient olefins utilizing tetra(n-butyl)ammonium peroxydisulfate
Jung, Jae Chul,Kim, Yong Hae,Lee, Kieseung
, p. 4662 - 4664 (2011)
Various electron-deficient olefins reacted readily with 1,3-dioxolane or 2-methyl-1,3-dioxlane in the presence of TBAP to afford the corresponding 1,3-dioxolanylated or 2-methyl-1,3-dioxolanylated products in a complete regioselective manner in good to ex
Synthesis of monoprotected 1,4-diketones by photoinduced alkylation of enones with 2-substituted-1,3-dioxolanes
Mosca, Raffaella,Fagnoni, Maurizio,Mella, Mariella,Albini, Angelo
, p. 10319 - 10328 (2007/10/03)
Photosensitized hydrogen abstraction from 2-alkyl-1,3-dioxolanes by triplet benzophenone gives the corresponding 1,3-dioxolan-2-yl radicals and these are trapped by α,β-unsatured ketones yielding monoprotected 1,4-diketones. With open chain ketones (3-buten-2-one and 4-penten-3-one) the yields are low and competitive pathways in part consume the radicals. With cyclic enones however, yields are good as tested with cyclopentenone, cyclohexenone and 4-hydroxy-cyclopentenone. More generally, this is a viable alternative for the synthesis of 1,4-diketones via radicals while the thermal initiation gives only low yield. The reaction cannot be extended to strongly stabilized radicals, such as the 2-phenyl-1,3-dioxolanyl radical.
