Chapter 1 C2O2S Ring platforms (pages 1–61):
Chapter 2 C2OS2 Ring structures (pages 62–66):
Chapter three C2S3 Ring structures (pages 67–75):
Chapter four C3OS Ring platforms (pages 76–312):
Chapter five C3S2 Ring structures (pages 313–610):
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Additional info for Chemistry of Heterocyclic Compounds: Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part 1, Volume 21
5% yield of the desired acetals. Fischer and Taube39 investigated several other reactions of glyoxal sulfate. Heating with a mixture of acetic acid and anhydride gave a 70% 26 C,O,S Ring Systems yield of glyoxal tetraacetate. Treatment with excess phenylmagnesium bromide gave a 44% yield of hydrobenzoin. ‘ 2 f 0 n 2 + C,HSMgBr -----+C,H, 6, H-CHC6H5 dH Acetone gave a product of unknown structure, while tertiary amines gave addition compounds which could not be purified. According to Reuter69a glyoxal sulfate reacts with aqueous sodium bisulfite to yield 1,2-dihydroxyethane-l, 2-disulfonic acid.
These a r e coplanar with methylene groups, and thus the same mechanism leads to ring contraction. /so H ---+ D- p H - o s o ;4 CHO + SO, 52 Foster, Hancock, and Overend40 studied the hydrolysis of 51 and 52. The trans sulfite 52 gave the frans diol under both acidic and basic conditions, apparently by sulfur-oxygen fission a s postulated for the 1, 3, 2-dioxathiolane 2-oxides (see section I A-3). The cis sulfite (Sl), however, reacted differently. Acid hydrolysis gave the cis diol, presumably by sulfur -oxygen cleavage, but alkaline hydrolysis gave mainly the frans diol, indicating nucleophilic displacement by hydroxide with carbon-oxygen cleavage.
P ec, c. -1 2 'SJ, C,O,S Ring Systems Presumably, the methyl p-glucoside product *Sa has a corresponding structure, According to Helferich and c o - w ~ r k e r s ~hydrolysis ~c of 47d with concentrated hydrochloric acid at 25" removes the methoxyl group, whereas sulfuric acid at 70" hydrolyzes the sulfate ring; the latter appears unreasonable. By the same reactions Bragg, Jones, and Turnerl9a showed that meth- yl &D-arabinOSide yields a 2,3-suIfate with a chlorine on (2-4. Sucrose gives a mixture of di- and trichlorodeoxysucrose disulfates.