Molecular transformations of unsaturated thiacrown ethers.
Unsaturated thiacrown ethers with 15, 18, and 21 members were oxidized to sulfoxides by the reaction with m-CPBA. The reaction with t-BuOCl at -20 degrees C also afforded sulfoxides, whereas the reaction at room temperature yielded cis-trans isomerized compounds. The cis-trans isomerized compound was also obtained by the photochemical reaction or by the reaction with NCS and NCP. Meanwhile, the reaction with NBS and NBP provided an acetal via 1,2-bridged bromonium intermediate.
Tsuchiya
Takahiro
T
Department of Chemistry, Graduate School of Sciences and Engineering, Tokyo Metropolitan University, Minami-ohsawa, Hachioji, Tokyo 192-0397, Japan.
Okada
Yosuke
Y
Shimizu
Toshio
T
Hirabayashi
Kazunori
K
Kamigata
Nobumasa
N
D047248:Crown Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010797:Phthalimides / Q000737:chemistry; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry; D013440:Sulfides / Q000737:chemistry*; D013454:Sulfoxides / Q000138:chemical synthesis* / Q000737:chemistry
D047248:Crown Compounds; D010797:Phthalimides; D013388:Succinimides; D013440:Sulfides; D013454:Sulfoxides