E. Block, T. Bayer, S. Naganathan
Mar 27, 1996
Citations
1
Influential Citations
69
Citations
Journal
Journal of the American Chemical Society
Abstract
Reduction (LiAlH4) of propyl 1-propynyl sulfide (8) to (E)-1-propenyl propyl sulfide ((E)-10), C−S cleavage (Li/NH3) to lithium (E)-1-propenethiolate (Li (E)-11), and reaction with MeSO2Cl gives (E,E)-bis(1-propenyl) disulfide ((E,E)-2); i-Bu2AlH reduction of 8 to (Z)-10 and reaction with Li/NH3 and then MeSO2Cl gives (Z,Z)-2 via Li (Z)-11. Reaction of MeSO2SR (R = Me (12a), n-Pr (12b), CH2CHCH2 (12c), CHCHMe (12d)) with K (E)-11 gives (E,Z)-2 from (Z)-12d; Li (E,Z)-11 gives alkyl (E)- and (Z)-1-propenyl disulfides (MeCHCHSSR, R = Me (3a), n-Pr (3b), CH2CHCH2 (3c)) from 12a−c, respectively. Oxidation at −60 °C of (E,E)-, (Z,Z)-, and (E,Z)-2 gives (E)-1-propenesulfinothioic acid S-(E)-1-propenyl ester ((E,E)-13, (E,E)-MeCHCHS(O)SCHCHMe) from (E,E)-2, (Z,Z)-13 from (Z,Z)-2, and ca. 2:1 (E,Z)-13)/(Z,E)-13 from (E,Z)-2. Warming (Z,Z)-13 gives (±)-(1α,2α,3β,4α,5β)-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5-oxide (1a), endo-5-methyl-exo-6-methyl-2-oxa-3,7-dithiabicyclo[2.2.1]heptane (14a), and exo-5-methyl-e...