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The reaction of dihydroxyacetone with ethanedithiol. Synthesis and x‐ray crystal structure of 1,4,7,10‐tetrathiaspiro[5.5]undecane
Author(s) -
Hamor T. A.,
Jones A. S.,
Jones R. H.,
Mcguigan C.,
Walker R. T.
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200108
Subject(s) - chemistry , undecane , monoclinic crystal system , cyclohexane , dihydroxyacetone , yield (engineering) , boron trifluoride , hydroxymethyl , crystal structure , crystallography , hydrochloric acid , medicinal chemistry , stereochemistry , organic chemistry , catalysis , materials science , glycerol , metallurgy
Reaction of dihydroxyacetone with an excess of ethanedithiol in the presence of 10 M hydrochloric acid gives 2,2‐di(hydroxymethyl)‐1,3‐dithiacyclopentane ( 1 ) in low yield. When boron trifluoride etherate is used instead of hydrochloric acid, the same reactants give 1,4,7,10‐tetrathiaspiro[5. 5]undecane ( 3 ). The structure of the latter was established by X ‐ray crystallography. The crystals are monoclinic, space group P2,/n, with a = 6.31(1), b = 21.57(2), c = 7.61(1)Å, β = 102.2(1)° and Z = 4, R = 0.038 for 2289 reflections. The two 1,4‐dithiane rings in 3 are significantly more puckered than normal cyclohexane rings. The uv spectrum of 3 is consistent with values reported for other sulphides and with the X‐ray structure.