عنوان

New methods of approach to the bicyclo[5:

TLets803064

New methods of approach to the bicyclo[5:

[Thesis]

Islam, Ahmad M.

3:0]decane system (1) ; Attempted synthesis of the indacenes (2)

University of Glasgow

1954

Thesis (Ph.D.)

1954

PART I. NEW METHODS OP APPROACH TO THE BICYCLO[5:3:0]DECANE SYSTEM. A. Condensation of propargyl bromide with 2-ethoxy-carbonylcycloalkanones furnishes products which, by hydration and subsequent ring closure, give bicyclic compounds with a five-membered ring fused to the ring of the starting material. e. g. Condensation of cycloheptanone with readily available acetylenic Mannich bases gives products which may be converted directly to bicyclo [5:3:0] decane derivatives by heating with formic acid-phosphoric acid e.g. C. Substituted cyclohexanones are subjected to ring expansion with a diazo-compound of such a nature that the resulting cycloheptanone possesses a side chain capable of condensing with the ring carbonyl group to yield bicyolo[5:3:0]decane derivatives directly. PART II. ATTEMPTED SYNTHESIS OP THE INDACENES. Attempted syntheses of the postulated quasi-aromatic hydrocarbons, symmetrical and assymmetrical indacenes have been investigated which involve dehydrogenation of the relevant hydroindacenes. The structure assigned to a supposed derivative of s-indacene reported in the literature has been shown to be erroneous.

Islam, Ahmad M.

University of Glasgow

p

[Thesis]

276903

a

Y