REACTION OF 2-CHLORO-1,3-ALKADIENYLPHOSPHONIC DIMETHYL ESTERS WITH ARENESELENENYL CHLORIDES

Abstract

Reaction of the 3-alkyl-2-chloro-1,3-alkadienylphosphonic dimethyl esters 1 with arenese-lenenyl chlorides affords mixtures of the 2,5-dihydro-1,2-oxaphosphole 2-oxides 2 and the 3-(1-arylselenoalkyl)-2-chloro-1,3-alkadienylphosphonic dimethyl esters 3. In contrast, the interaction of the 2-chloro-2-(1-cyclohexenyl)ethenephosphonic dimethyl ester 1d with areneselenenyl chlorides occurs with six-membered heterocyclization and formation of the 5-arylseleno-4-chloro-5,6,7,8,9,10-hexahydrobenz-2H-1,2-oxaphosphorine 2-oxides 4. The oxidative elimination of the areneselenenyl moiety in the bicyclic compounds 4 yields the 4-chloro-7,8,9,10-hexahydrobenz-2H-1,2-oxaphosphorine 2-oxides 5.

Key Words:

• 2-chloro-1,3-alkadienylhoshonk dimethyl esters areneselenenyl chlorides
• 2,5-dihydro-1,2-oxaphoshole 2-oxides
• 3-(1-arylselenoalkyl)-2-chloro-1,3-alkadienylphosptonic dimethyl esters
• 5,6,7,8,9,10-hexahydrobenz-2H-1,2-oxaphosphorine 2-oxides
• oxidative elimination
• 7,8,9,10-hexahydrobenz-2H-1,2-oxaphosphonne 2-oxides