INTRODUCTION β-hydroxy thiocyanates play an important role in the realm of organic chemistry, such as biological, pharmaceutical and agricultural chemistry 1 . In the recent decade, these compounds were prepared by the reaction of different epoxides with NH 4 SCN in the presence of various catalysts and different condition. Epoxides or oxiranes are useful and important synthetic intermediates in organic synthesis. 2 Their inherent polarity and high angle strain of three-membered ring make them susceptible to react with a wide variety of reagents, including reducing agents, oxidizing agents, ORIENTAL JOURNAL OF CHEMISTRY www.orientjchem.org ISSN: 0970-020 X CODEN: OJCHEG 2011, Vol. 27, No. (4): Pg. 1531-1553 Est. 1984 An International Open Free Access, Peer Reviewed Research Journal Some Versatile and Efficient Methods for the Regioselective Ring Opening of Epoxides to Corresponding β-Hydroxy Thiocyanates FARIBA HEIDARIZADEH¹ and SOMAYEH ELAHI² ¹Department of Chemistry, Faculty of Science, Shahid Chamran University, Ahvaz (Iran). ²Abadan Branch, Islamic Azad University, Abadan (Iran). *Corresponding author: E-mail: heidarizadeh@scu.ac.ir (Received: April 12, 2011; Accepted: June 04, 2011) ABSTRACT In this review, was reported some methods for the preparation of â-hydroxy thiocyanates, which are considered as an important class of compounds often used as key intermediates in agricultural and pharmaceutical chemistry. Key words: Regioselectivity, Ring opening, Thiocyanohydrin, Epoxide, β-Hydroxythiocyanate, Solid phase, Liquid phase. electrophiles, nucleophiles, acids, and bases 3-4 . The ring opening of epoxides with different nucleophiles is an attractive subject in organic transformations 5 . Between these nucleophiles, the reaction of thiocyanate ion with epoxides, in the absence or in the presence of catalyst is a widely studied and suitable method for the preparation of thiiranes 6-13 . The formation of thiiranes from the reaction of epoxides and thiocyanate ion has been proposed to occur through the intermediacy of the corresponding β -hydroxy thiocyanate (I) (Scheme 1), but this intermediate has not been isolated due to its rapid conversion to the corresponding thiirane 11-14 .