The mixed diol–dithiol 2,2-bis(sulfanylmethyl)propane-1,3-diol: characterization of key intermediates on a new synthetic pathway

Simmons, TR, Pickett, CJ and Wright, JA (2011) The mixed diol–dithiol 2,2-bis(sulfanylmethyl)propane-1,3-diol: characterization of key intermediates on a new synthetic pathway. Acta Crystallographica Section C: Crystal Structure Communications, 67 (1). 01-05. ISSN 0108-2701

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Abstract

A new synthetic route to 2,2-bis(sulfanylmethyl)propane-1,3-diol, (II), is described starting from the commercially available 2,2-bis(hydroxymethyl)propane-1,3-diol. The structures of two intermediates on this route are described. 5,5-Dimethenyl-2,2-dimethyl-1,3-dioxane bis(thiocyanate) (systematic name: {[5-(cyanosulfanyl)-2,2-dimethyl-1,3-dioxan-5-yl]sulfanyl}formonitrile), C10H14N2O2S2, (X), crystallizes in the space group P21/c with no symmetry relationship between the two thiocyanate groups. There is a short intramolecular NS contact for one thiocyanate group, while the second group is positioned such that this type of interaction is not possible. 1,3-(Hydroxymethyl)propane-1,3-diyl bis(thiocyanate), C7H10N2O2S2, (XI), also features a single short NS contact in the solid state. Hydrogen bonding between two molecules of compound (XI) results in the formation of dimers in the crystal, which are then linked together by a second hydrogen-bond interaction between the dimers. In addition, the structures of two intermediates from an unsuccessful alternative synthesis of (II) are reported. 2,2-Bis(chloromethyl)propane-1,3-diol, C5H10Cl2O2, (VI), crystallized as an inversion twin with a minor twin fraction of 0.43 (6). It forms a zigzag structure as a result of intermolecular hydrogen bonding. The structure of 9,9-dimethyl-2,4,8,10-tetraoxa-34-thiaspiro[5.5]undecan-3-one, C8H14O5S, (VII), shows evidence for a weak SO contact with a distance of 3.2529 (11) Å.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Rhiannon Harvey
Date Deposited: 21 Mar 2012 16:15
Last Modified: 21 Sep 2020 23:27
URI: https://ueaeprints.uea.ac.uk/id/eprint/38424
DOI: 10.1107/S0108270110049371

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