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Highly facile biomimetic regioselective ring opening of epoxides to halohydrins in the presence of β-cyclodextrin

M. Arjun Reddy, K. Surendra, N. Bhanumathi and K. Rama Rao*

*Organic Chemistry Division 1, Indian Institute of Chemical Technology, Hyderabad 500 007, India, Email: ramaraokiict.ap.nic.in

M. Arjun Reddy, K. Surendra, N. Bhanumathi, K. Rama Rao, Tetrahedron, 2002, 58, 6003-6008.

DOI: 10.1016/S0040-4020(02)00614-2


Abstract

Highly regioselective ring opening of epoxides to halohydrins has been carried out in impressive yields with hydrogen and lithium halides in presence of β-cyclodextrin using water as solvent.

Epoxide Reagent Product Yield (%, isol.)
HCl
HBr
HI
LiCl
LiBr
LiI
96
90
89
89
85
82
HCl
HBr
HI
LiCl
LiBr
LiI
88
90
84
78
84
75

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Highly Efficient Regioselective Ring Opening of Aziridines to β-Haloamines in the Presence of β-Cyclodextrin in Water

N. S. Krishnaveni, K. Surendra, M. Narender, Y. V. D. Nageswar, K. R. Rao, Synthesis, 2004, 501-502.


Key Words

Epoxides, Bromohydrins, Chlorohydrins, Iodohydrins, Hydrogen Halides, Lithium Halides, Cyclodextrin, Supramolecular Catalysis


ID: J72-Y2002-050