CONVERSION OF EPOXIDES INTO 2-HYDROXYETHYL THIOCYANATES WITH NH₄SCN IN THE PRESENSE OF 2,6-BIS[2-(O -AMINO PHENOXY)METHYL]-4-BROMO-1-METHOXYBENZENE (BABMB) AS CATALYST

Abstract

A convenient and efficient procedure for the ring-opening of 1,2-epoxyethanes with ammonium thiocyanate in the presence of 2,6-bis[2-(o -aminophenoxy)methyl]-4-bromo-1-methoxybenzene (BABMB) is described. In this study, a reagent and conditions have been discovered with which the individual 2-hydroxyethyl thiocyanates can be synthesized in high yield and with more than 90% regioselectivity. Thus, several 2-hydroxyethyl thiocyanates, useful intermediates toward biological-active molecules, are easily obtained in very good yields.

Keywords:

• Ammonium thiocyanate
• catalyst
• epoxide
• podand diamine
• thiocyanohydrin

I gratefully acknowledge the support of this work by the Persian Gulf University Research Council. Also, I thank Miss N. Moghtamed Rad for running the UV spectra.

Notes

^a Determined by GC.

^b In the presence of excess of NH₄SCN.

^c 35% of the corresponding thiirane was obtained.