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Chemistry of Heterocyclic Compounds: Multi-Sulfur and Sulfur

Content material:
Chapter 1 C2O2S Ring platforms (pages 1–61):
Chapter 2 C2OS2 Ring platforms (pages 62–66):
Chapter three C2S3 Ring structures (pages 67–75):
Chapter four C3OS Ring structures (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

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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. So0 ~ 100% 0 H-CHSW 3 ~ bH Anthrone (44) is reported to react with glyoxal sulfate to form a yellow dye. 61 IV. C,02S-C,0 FUR0 [3,4-d]-1,3,2-DIOXATEIOLE(Ma) Brimacombe, Foster, and co-w0rkers,1~~ prepared the only member of this series, presumably cis-tetrahydrofuro [3, 4 4 -I, 3, 2-dioxathiole 2, 2-dioxide (44b), from 1,4-anhydroerythritol’and thionyl chloride.

It melts at 106-108°. V. CzO$bC,S 44b THJENO [3,4-dJ-1,3,2-DIOXATHIOLE (45) 45 [For references, see pp. ne dioxide and thionyl chloride. A lower yield was obtained in the presence of pyridine. The broad melting point of 45a, 129-136", would seem t o indicate t h a t some isomerization took place under these reaction conditions. VI. C,O,S-C, 3aH-CYCLOPENTA-1,3,2-DIOXATEIOLE (46) 46 (RRI 871) There are several representatives of this ring system. p. criis -2-chlorocyclopentanol was formed a s a by-product.

The broad melting point of 45a, 129-136", would seem t o indicate t h a t some isomerization took place under these reaction conditions. VI. C,O,S-C, 3aH-CYCLOPENTA-1,3,2-DIOXATEIOLE (46) 46 (RRI 871) There are several representatives of this ring system. p. criis -2-chlorocyclopentanol was formed a s a by-product. 1: the formation of the sulfite. h:oride in dioxane gives the chlorohydrin with retention of configuratiolz, in agreement with the results of Tchoubarsl on the correspondinj cyclohexane derivatives; the mechanism is discussed in section VIII A.

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