A novel 3,4-bis(sulfenyl)- or 4-selenenyl-3-sulfenylpenta-2,4-dienylation of aldehydes using 4-ethoxy-1,2-bis(sulfenyl)- or 1-Selenenyl-2-sulfenyl-buta-1,3-dienyl lithiums.
3,4-Dichalcogenopenta-2,4-dienylation of aldehydes proceeded in good to high yields using 4-ethoxy-1-(benzenesulfenyl)-2-(methanesulfenyl)- (5), 4-ethoxy-1,2-bis(benzenesulfenyl)but-1,3-diene (6), and 1-selenenyl derivatives 7 and 8. This novel four-carbon homologation could be applied to a synthesis of 3,4,7,8-tetrakis(benzenesulfenyl)-10,10-dimethylundeca-2,4,6,8-tetraenal (20).
Yoshimatsu
Mitsuhiro
M
Department of Chemistry, Faculty of Education, Gifu University, Japan. yoshimae@cc.gifu-u.ac.jp
Matsuura
Yasutaka
Y
Gotoh
Kohei
K
D000447:Aldehydes / Q000138:chemical synthesis*; D008094:Lithium / Q000737:chemistry*; D018036:Selenium Compounds / Q000138:chemical synthesis*
D000447:Aldehydes; D018036:Selenium Compounds; D008094:Lithium