NICKEL (II) CATALYZED SUBSTITUTION OF HALOGENS IN 1-HALO-1-CHALCOGENE ALKENES BY CHALCOGENATE ANIONS

Abstract

Bis(bipyridine)nickel (II) bromide catalyzes the substitution of chlorine, bromine and iodine in 1-halo-1-chalcogene alkenes [RCH=CX(YR¹), R=C₆H₅, n-C₄H₉; R¹=CH₃, C₆H₅: X=Cl, Br, 1: Y=S, Se] by phenylselenolate and phenyltellurolate anions leading to the S-Se, Se-Te and Se-Se asymmetrically substituted ketene chalcogeneacetals [RCH=C(YR¹)Y¹ C₆H₅] under mild conditions (30–70°C, 1 atm) and in good yields (80–95%) within a short reaction time (10–60 min). The following compounds were prepared: C₆H₅CH=C(SeCH₃)SeC₆H₅, C₆H₅CH=C(SCH₃)SeC₆H₅, n-C₄H₉CH═C(SeH₃)SeC₆H₅, n-C₄H₉CH=C(SCH₃)SeC₆H₅, n-C₄H₉CH=C(SC₆H₅)Se₆H₅, n-C₆H₅ CH=C(SeCH₃) TeC₆H₅.

Key Words:

• 1-halo-1-chalcogenealkenes
• halogen substitution
• nickel catalyst
• ketene chalcogeneacetals