67532-06-3Relevant academic research and scientific papers
Reaction of [(Z)-1-bromo-1-alkenyl]dialkylboranes with N-halogeno compound in THF-DMF: A novel synthesis of 1,2-disubstituted (E)-vinyl bromides
Hoshi, Masayuki,Shirakawa, Kazuya
, p. 2595 - 2598 (2000)
DMF-induced reaction of [(Z)-1-bromo-1-alkenyl]dialkylboranes with an N- halogeno compound results in 1,2-migration of an alkyl group from the dialkylboryl group to the α-carbon atom without elimination of the bromine atom, followed by β-elimination to provide 1,2-disubstituted (E)-vinyl bromides stereoselectively in good yields. (C) 2000 Elsevier Science Ltd.
Reaction of (Z)-1-bromoalk-1-enyldialkylboranes with DMSO: Regio- and stereo-selective formation of internal (E)-alkenyl bromides
Hoshi, Masayuki,Tanaka, Hideyuki,Shirakawa, Kazuya,Arase, Akira
, p. 627 - 628 (2007/10/03)
Treatment of (Z)-1-bromoalk-1-enyldialkylboranes 1 with DMSO results in 1,2-migration of an alkyl group from the boron to the α-carbon without elimination of bromine to give internal (E)-alkenyl bromides 2 with excellent stereoselectivity (>99%).
The Reactions of (1-Halo-1-alkenyl)dialkylboranes with Lead(IV) Acetate or (Diacetoxyiodo)benzene. A Stereoselective Synthesis of 1-Halo-1,2-dialkylethylenes
Masuda, Yuzuru,Arase, Akira,Suzuki, Akira
, p. 1652 - 1655 (2007/10/02)
The reaction of (1-halo-1-alkenyl)dialkylboranes with lead(IV) acetate or (diacetoxyiodo)benzene was studied. (1-Bromo-1-alkenyl)dialkylboranes gave 1-bromo-1,2-dialkylethylenes.When alkyl groups on the boron atom of vinylboranes were bulky or the reaction temperatures were low, Z-isomers were afforded, whereas when alkyl groups on the boron atom were small or the reaction temperatures were relatively high, E-isomers were afforded as the main products. (1-Chloro-1-alkenyl)dialkylboranes gave (Z)-1-chloro-1,2-dialkylethylenes regardless of the reaction conditions. (1-Iodo-1-alkenyl)dialkylboranes failed to give satisfactory yields of 1-iodo-1,2-dialkylethylenes.
