Studies in the Phenanthrene Series. XXIII. Synthesis of Acyl Compounds Derived from 2-Hydroxy-9,10-dihydrophenanthrene

Abstract

This investigation was undertaken with the aim of synthesizing compounds from which, because of their structural similarity to oestrone (I), some oestrogenic activity might be expected.2 2-Hydroxy-9,10-dihydrophenanthrene (II) appeared

Chemistry of enol silyl ethers. 5. A novel cycloaromatization reaction. Regiocontrolled synthesis of substituted methyl salicylates

“…Tak-Hang Chan* and Peter Brownbridge Contribution from the Department of Chemistry, McGill University, Montreal, Quebec, Canada H3A 2K6. Received July 30,1979 Abstract: A new method of constructing six-membered rings, involving the condensation of two three-carbon units, one with two nucleophilic sites and the other containing two electrophilic sites, is reported. The regiochemistry of the reaction is controlled by the differential reactivities of these sites.…”

General Methods of Preparing Chromones

“…An o-acyloxyphenylalkanone (79) is probably an intermediate in the reaction; it may undergo a Baker-Venkataraman rearrangement (Section 11.2) to yield an o-hydroxydiketone that loses water to give a chromone (80) or (81). When R1 is a substituent other than hydrogen, the chromone (81) is formed, but when R' = H, either (80) or (82) or a mixture of both may be obtained. Alternatively, an intramolecular aldol condensation and elimination of water may convert the ester (79) into a coumarin.…”

Cyclic Polyolefins. XXIX. Cycloöctatetraene Derivatives from Copolymerization and Side Chain Modification1

“…), nud 1.4443. 5 Copolymerization of 20 g. of 4-pentyn-l-ol with acetylene by the general procedure described previously1 resulted in an absorption of 1200 p.s.i. of acetylene and an increase in weight of 171 g. in 8 hours at 84-92°.…”