ADDITION REACTION OF SULFUR DICHLORIDE TO FUNCTIONALIZED IMINES DIRECTED TOWARD HETEROCYCLIC SYNTHESIS |
| |
| Authors: | Mitsuo Komatsu Nobuyuki Harada Hiroshi Kashiwagi Yoshiki Ohshiro Toshio Agawa |
| |
| Affiliation: | Department of Applied Chemistry, Faculty of Engineering , Osaka University , Yamada-oka 2-1, Suita, Osaka, 565, Japan |
| |
| Abstract: | Abstract Although it was shown that the reactions of sulfur dichloride (SCl2) with the imines la-c or with the azine 14 gave rise to very unstable 1 : 1 adducts, 1-aza- and 2-azabutadienes, 5 and 10, reacted with SCl2 to afford the isothiazoles 6 and the thiazoles 11, respectively, in high yields. Addition of SCl2 to heterocumulenes was also studied and the ketenimines 16 and diphenylketene 27 gave 1 : 1 adducts which were applied to heterocyclic synthesis as bifunctional reagents. Addition of SCl2 to these compounds was investigated by monitoring the reactions by 13C nmr spectroscopy. |
| |
| Keywords: | Synthesis o-hydroxyaryl dialkyl phosphine oxides substituent effect 31P NMR chemical shifts molecular mechanics |
|
|
