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Green Regioselective Azidolysis of Epoxides Catalyzed by Multi‐Site Phase‐Transfer Catalyst
Author(s) -
Kiasat Ali Reza,
Mirzajani Roya,
Shalbaf Haji,
Tabatabaei Tahereh,
FallahMehrjardi Mehdi
Publication year - 2009
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200900088
Subject(s) - chemistry , regioselectivity , catalysis , chloride , cyanide , epoxide , phase transfer catalyst , phase (matter) , melamine , ring (chemistry) , organic chemistry
A facile synthesis of 1,2‐azidoalcohols from their epoxides using α,α',α”‐ N ‐hexakis(triethylammoniummethylene chloride)‐melamine as a multi‐site phase‐transfer catalyst in water was developed. By this eco‐friendly and highly atom‐economic method, a variety of 1,2‐azidoalcohols was obtained in high yields with excellent regioselectivity and in short reaction times. Application of this six‐site PTC in the ring opening of epoxides by cyanide, acetate and chloride anions was also studied. The catalyst can be recovered after completion of the reaction and can be recycled without affecting the catalytic property.