83587-47-7Relevant academic research and scientific papers
3,5-Bis(trifluoromethyl)phenyl sulfones in the Julia-Kocienski olefination - Application to the synthesis of tri- and tetrasubstituted olefins
Alonso, Diego A.,Fuensanta, Monica,Najera, Carmen
, p. 4747 - 4754 (2007/10/03)
3,5-Bis(trifluoromethyl)phenyl (BTFP) sulfones 8a-d are successfully employed in the modified Julia olefination reaction with carbonyl compounds employing phosphazene base P4-tBu at room temp. in THF, affording tri- and tetrasubstituted olefins in good yi
Efficient preparation of trisubstituted alkenes using the SmI2 modification of the Julia-Lythgoe olefination of ketones and aldehydes
Markó, István E,Murphy, Fiona,Kumps, Lucien,Ates, Ali,Touillaux, Roland,Craig, Donald,Carballares, Santiago,Dolan, Simon
, p. 2609 - 2619 (2007/10/03)
High yields of di- and tri-substituted alkenes are obtained by a modification of the Julia-Lythgoe olefination reaction involving the in situ capture of intermediate β-alkoxy-sulfones by benzoyl or trimethylsilyl chloride, followed by SmI2-mediated reductive elimination. This novel protocol also provides a connective preparation of dienyl ethers, which are important partners in Diels-Alder cycloadditions.
Reactions of 1,1-Dihaloalkenes with Triorganozincates: A Novel Method for the Preparation of Alkenylzinc Species Associated with Carbon-Carbon Bond Formation
Harada, Toshiro,Katsuhira, Takeshi,Hara, Daiji,Kotani, Yasuo,Maejima, Keiji,et al.
, p. 4897 - 4907 (2007/10/02)
Lithium trialkylzincates react with 1,1-dibromoalkenes 1 and 1-bromo-1-chloroalkenes 2 at -85 deg C in THF to give 1-bromoalkenes 5 and 1-chloroalkenes 7, respectively, upon hydrolysis.The intermediate (1-haloalkenyl)zincates 4 and 6 are stable at low temperature but, when allowed to warm to 0 deg C, they undergo a 1,2-alkyl migration reaction to afford alkenylzinc species 10.A variety of alkylation products 11 are obtained by the hydrolysis of 10.In the presence of (Ph3P)2Pd (5 molpercent), alkenylzinc species 10 react smoothly with organic halides (AcCl, EtOCOCl, CH2=CH(Me)Br, PhBr) to yield the corresponding coupling products 13-16.
