53608-85-8Relevant academic research and scientific papers
One-pot desymmetrizing hydroformylation/carbonyl ene cyclization process: Straightforward access to highly functionalized cyclohexanols
Bigot, Aurelien,Breuninger, Daniel,Breit, Bernhard
supporting information; experimental part, p. 5321 - 5324 (2009/06/06)
(Chemical Equation Presented) Rapid access to highly functionalized alkylidene cyclohexanols through a one-pot desymmetrizing hydroformylation/ carbonyl ene cyclization starting from simple bisalkenylcarbinols is reported. Mechanistic insight into the carbonyl ene reaction is given, highlighting the importance of hyperconjugative substituent effects.
Neighbouring-group influence on the ring opening of some 2-alkyl-1,1,2-tribromocyclopropanes under phase-transfer conditions
Sydnes, Leiv K.,Alnes, Karl F. S.,Erdogan, Natalia
, p. 1737 - 1749 (2007/10/03)
Several 2-alkyl-1,1,2-tribromocyclopropanes were treated with sodium hydroxide and ethanol under phase-transfer conditions. Ring opening gave mixtures of the corresponding acetylenic diethyl ketals and acetals. When the steric bulk of the alkyl substituent was increased acetal formation dominated, and in the case of 1,1,2-tribromo-2-(tert-butyl)cyclopropane, the acetal was formed as the only product. Springer-Verlag 2005.
Selective Mono- and Polymethylene Homologations of Copper Reagents Using (Iodomethyl)zinc Iodide
Sidduri, AchyuthaRao,Rozema, Michael J.,Knochel, Paul
, p. 2694 - 2713 (2007/10/02)
A wide range of unsaturated aryl-, alkenyl-, alkynylcopper compounds can be selectively homologated by a methylene unit using (iodomethyl)zinc iodide or bis(iodomethyl)zinc.These reactions allow the generation of mixed allylic zinc-copper compounds which can be efficiently trapped with carbonyl compounds.An application to a general preparation of functionalized α-methylene-γ-butyrolactones is described.The homologation of alkynylcoppers with (iodomethyl)zinc iodide allows a one-pot preparation of propargylic copper reagents which in the presence of a carbonyl compound provide various homopropargylic alcohols in excellent yields.In the absence of an electrophile, a clean quadruple methylene homologation of alkynylcoppers occurs to furnish dienic copper reagents.The homologation of other types of copper reagents is also possible, and carbanions at the α-position to amines as well as homoenolates of aldehydes or ketones can also be prepared by this method.
New reagents for radical allylations
Curran,Yoo
, p. 6931 - 6934 (2007/10/02)
Three reagents are introduced for radical allylations: 3-phenylthio-2-bromopropene, 2,3-bis(trimethylstannyl)propene, and 3-tris(trimethylsilyl)silylthiopropene.
