2-(2-AMINOALKENYL)-4,5-DIHYDRO-4-THIOXO-1,3,4-THIAZAPHOSPHOLE

Abstract

Phenyl isothiocyanato-chlormethylthiophosphonate and enamines in the presence of triethylamine condense to give the title compounds 6 and 8. An X-ray crystal structure investigation of 6a shows a strong influence of the 2-(2-aminoalkenyl) substituent which results in an alternating shortening and elongation of both single and double bonds throughout the system. The effect is definitely more pronounced than that of an NH₂ or SR substituent.

Key Words:

• 2-Carbosubstituted 1,3,4-thiazaphospholines
• isothiocyanato-chlormethylthiophosphonates
• cyclization