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2 Polish Journal of Chemistry

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Addition of Diazomethane to Phosphonodithioformates and Reactions of Phosphonylated Thiocarbonyl S-Methylides

Urbaniak K., Mlostoń G., Gulea M., Masson S., Heimgartner H.

Polish Journal of Chemistry

2005

Vol. 79 / nr 9

1483-1494

The reaction of phosphonodithioformates 14 with diazomethane at -60 graduate C yielded 2,5-dihydro-1,3,4-thiadiazoles 15 as unstable intermediates. Their structure was evidenced by the base-catalyzed elimination of methylsulfane leading to 1,3,4-thiadiazole- 2-phosphonates. At ca. -35 graduate C, thermal decomposition of 15 by N2-elimination led to reactive thiocarbonyl S-methylides 17. In the absence of trapping reagents, these 1,3-dipoles undergo a head-to-head dimerization leading to 1,4-dithianes 18. An intermediate zwitterionic dimer 19 was detected by 31P NMR spectroscopy. The initially formed thiocarbonyl S-methylide 17 as well as an open-chain zwitterionic dimer 20 was intercepted by methanol. Stable interception products were also obtained with S- and N-nucleophiles.

New Functionalized Derivatives of Sulfur- and Oxygen-Containing Hexacyclic Cage Compounds

Romański J., Marchand A.

Polish Journal of Chemistry

2004

Vol. 78 / nr 2

223-230

Several new sulfur- and oxygen-bridged hexacyclic cage compounds have been obtained via transannular cyclization of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (1). Thus, cage-annulated thiapodands 9 and 10 were prepared via reaction of ditosylate 6 with 2-mercaptoethylamine (7) or 2-mercaptoethanol (8), respectively. Other ditosylate 11 was reacted with thiourea to afford the corresponding dimercapto podand 12. An optically active podand (R,R)-14 was prepared in similar fashion by reacting ditosylate 6 with (R)-2-amino-1-butanol (R)-(13). Functionalized 4-thiahexacyclo[ 5.4.1.0.02,6.03,10 .05,9.08,11]dodecanes 17a-band18a-b were prepared via reactions of 1 with 2-chloro- (15) or 2-bromoethanol (16), respectively in the presence of H2S(g) and HCl(g). The corresponding reaction of 1 with 2 equivalents of 8 produced the corresponding bisthioacetal 20, which subsequently was changed into a spiro-cage-annulated dithiacrown ether 22.