Bromohydrin formation in dimethyl sulfoxide

DR Dalton, VP Dutta, DG Jones

Index: Dalton,D.R. et al. Journal of the American Chemical Society, 1968 , vol. 90, # 20 p. 5498 - 5501

Full Text: HTML

Citation Number: 168

Abstract

Abstract: A number of olefins have been converted to their respective bromohydrins by the use of N-bromosuccinimide (NBS) and moist dimethyl sulfoxide (DMSO). The mechanism of this stereospecific transformation has been elucidated and general trends have been observed. These include (1) Markovnikov orientation of addition in the absence of steric restrictions;(2) failure of the reaction with highly hindered olefins and olefins bearing ...

Antibacterial benzisoxazolones. An unusual rearrangement pro...

[Wierenga, Wendell; Harrison, Allen W.; Evans, Bruce R.; Chidester, Connie G. Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 438 - 442]

Synthesis of β-adrenergic blockers (R)-(−)-nifenalol and (S)...

[Kapoor, Munish; Anand, Naveen; Ahmad, Khursheed; Koul, Surrinder; Chimni, Swapandeep S.; Taneja, Subhash C.; Qazi, Ghulam N. Tetrahedron Asymmetry, 2005 , vol. 16, # 3 p. 717 - 725]

Allyltin tribromide: A versatile reagent involved in the rin...

[Chen, Guohong; Wang, Xin; Jin, Xiaoqian; Liu, Lingyan; Chang, Weixing; Li, Jing Science China Chemistry, 2010 , vol. 53, # 6 p. 1294 - 1301]

Exploration of the biocatalytic potential of a halohydrin de...

[Lutje Spelberg, Jeffrey H.; Tang, Lixia; Van Gelder, Marc; Kellogg, Richard M.; Janssen, Dick B. Tetrahedron Asymmetry, 2002 , vol. 13, # 10 p. 1083 - 1089]

Remarkable difference of chemoselectivity in the reduction o...

[Shibata, Ikuya; Nakamura, Kenji; Baba, Akio; Matsuda, Haruo Tetrahedron Letters, 1990 , vol. 31, # 44 p. 6381 - 6384]