CYCLOADDITION OF METAL OXYALLYL CATIONS TO ANTHRACENES

Abstract

Cycloaddition of Metal Oxyallyl Cations to Anthracenes

Benzoctamine (A) and Maprotilinc (B) arc ncuroleptics which arc used clinically for

the treatment of mental disorders such as schizophrenia and depression 40 41 •

NHCH 3

Cycloaddition of oxyallyl cations to anthracenes offered a direct access to a variety of higher homologucs and analogues. Tctrabromoacetone (1) was allowed to cycloadd to anthracene (.8) in the presence of Zn-Cu couple in dioxane at sooc giving two isomeric cycloadducts 9a-b , which also, prepared by using the ultrasonic method. On application of the Zn-Cu I BSA I Benzene I Ultrasound, the tribromocycloadduct

lQ was formed in 42% and the dibromocycloadduct 9b in 5% yield.

(1)(2) (3) 0 2• 9b Br Br 00:) u, Br h

R

( 4) +

1!! 2h

(I) Zn-Cu I Mc,SiCI I Dioxane, 80°C, 20 h, 15.4%. (2) Zn-Cu I Me 1SiCI I Dioxane I Ultrasound, I0-20°C, 8 h, 22.1%. (3) Zn-Cu I Dioxane I Ultrasound, I0-20oC, 8 h, 28%.. (4) Zn-Cu I BSA I Benzene I Ultrasound, I0-20°C, 6 h. '