Reactivity of the double bond in Coumarins and related unsaturated Carbonyl compounds. Part VII. Action of mercuric acetate on hydroxy and 4-methyl coumarins

Abstract

The action of mercuric acetate in methyl alcoholic solution on (1) umbelliferone, (2) 4-methylumbelliferone and (3) 4: 7-dimethylcoumarin has been investigated. With umbelliferone addition at the double bond and substitution in positions 6 and 8 take place whereas in the case of its 4-methyl derivative position 8 alone is mercurated to yield a monoacetoxymercuri-compound. In regard to the last compound the reaction stops with addition at the double bond and mercuration of the 6th position, the position 8 escaping the attack of the reagent. It is concluded that owing to the influence of the substitutent groups the reactivity of the three active centres of the coumarin molecule are differently affected.