Chemistry of Heterocyclic Compounds: Multi-Sulfur and Sulfur

Content material:
Chapter 6 C2O2S2 Ring structures (pages 611–625):
Chapter 7 C2S4 Ring structures (pages 626–632):
Chapter eight C3O2S Ring platforms (pages 633–674):
Chapter nine C3OS2 Ring structures (pages 675–688):
Chapter 10 C3S3 Ring structures (pages 689–773):
Chapter eleven C4 OS Ring structures (pages 774–951):
Chapter 12 C4S2 Ring platforms (pages 952–1252):
Chapter thirteen Ring structures Containing Selenium and Tellurium (pages 1272–1346):

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Extra info for Chemistry of Heterocyclic Compounds: Multi-Sulfur and Sulfur and Oxygen Five- and Six-Membered Heterocycles, Part 2, Volume 21

Example text

76,3952 (1954). Bordwell, F. ,and M. L. Peterson, J. , 18,3957 (1954). Breslow, D. , R R H w g h , and J. T. Fairclough, J. A m Chem. ~,5361 (1954). , and R R Haugh, J. A m Chem. , 79,5000 (1957). , J. Am. Chem. , 67,220 (1945). ,J. Am. ,71, 1769 (1949). ,and k M. S. Patent 2,839,573 (1958); Ger. Patent 1,059,443 (1959). Daimler, K , and K. Platz (to L G. S. Patent 1,913,794 (1933). French Patent 716,914 (1931);Chem. 26,2751 (1932). Ger. Patent 550,572(1930);Chem. Abstracts, 4828 (19SZ). Brit.

An attempt to isolate the postulated intermediate, 3-chlorobutylsulfuric acid @ti),by carrying out the hydrolysis in the presence of potassium chloride was unsuccessful. Other acidic reagents react to cleave the sulfate ring of 4-methyl-l, 3,2-dioxathiane [For references, see pp. ) 653 Chapter 8 c 2,2-dioxide (31) predominantly at the secondary carbon atom, Hydrobromic acid yields 3-bromo-1-butanol, although in low yield. Alcohols react to form 3-alkoxy-1-butanols and 1,3-dialkoxybutanes, the former product showing that cleavage takes place initially at the secondary carbon atom Phenol yields a compound formulated a8 Il-methylchroman (311, presumably via the intermediate 3-phenoxybutylsulfuric acid (36).

Slundecane 3, 3,9,9-tetroxide (43), melts at 202" with decomposition. Although they gave no details of its preparation, it may be assumed that it was made by permanganate Oxidation of the disulfite. 43 2 N - l , S , Z-DiOlxathiin (44) He:3 H 'q3 H2 44 (RRI 219) In 1916 Schroeters@reported that the reaction of the dimethyl ester of dimethylacetonedicarboxylic acid with cold fuming sulfuric acid gives a product melting at 67-68', which he formulated as a cyclic sulfate, 4-0x0-5-methyl-6- (1-carbomethoxy- l-ethyl)-&Z-l,3, 2-dioxathiin 2, 2-dioxide (45).

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