Efficient Routes for the Synthesis of Dinaphthosulfide (BINOL Derivatives) and Dibenzosulfide Aza Podands Containing Ethanolamine

Authors: Rostami, Esmael¹; Heidaryan, Davood²; Fattahi, Hanif²; Shockravi, Abbas²; Zarei, Mehdi²; Rakhshanderu, Farokh²

Source: Phosphorus, Sulfur, and Silicon and the Related Elements, Volume 184, Number 7, July 2009 , pp. 1924-1934(11)

Publisher: Taylor and Francis Ltd

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Abstract:

Four new dinaphthosulfide and dibenzosulfide aza podands were synthesized. The synthesis of these podands was performed under three different reaction conditions: 1) diester, K2CO3, methanol, and RT; 2) diester, ethanolamine, and microwave (MW); and 3) diacid dichloride, ethanolamine, Et3N, CH2Cl2, RT. Two kinds of diester (dinaphthosulfide and dibenzosulfide) were used for the preparation of dihydroxy podands. These dihydroxy podands were reacted with thionyl chloride to afford dichloro podands. The second route gave excellent yields of dihydroxy podands. Dichloro podands are more soluble than dihydroxy podands in conventional solvents such as methanol, chloroform, and acetonitrile.

Keywords: Aza podand; 2-chloro ethanolamine; dibenzosulfide; dinaphthosulfide; synthesis

Document Type: Research article

DOI: http://dx.doi.org/10.1080/10426500802417059

Affiliations: 1: Faculty of Science, Department of Chemistry, Bushehr Payamenoor University, Bushehr, Iran 2: Faculty of Chemistry, Tarbiat Moallem University (Teacher Training University), Tehran, Iran

Publication date: 2009-07-01