Isomerically pure cis,cis,trans-1-pheny1-1,3,5-
heptatriene was prepared and cyclized. Ring closure
was followed by a 1,5 hydrogen shift, and the only product
observed was 1-phenyl -6-methyl -1,3-cyclohexadiene.
Rough first order rate constants for thermolysis and
the hydrogen shift were determined. Kinetic estimates
indicate that the report of disallowed product in a...
3-Methyl-2,4-dioxabicyclo [3.3.1] nonane and 7-hydroxy-3-methyl-2, 4-dioxabicyclo [3.3.1] nonane were synthesized by the
method of Croxall, Glavis and Neher, although in low yields.
The structure of both compounds was proven by analytical
methods and analysis of their spectral properties.
Tentative configuration of C-3 in both compounds was
assigned on the assumption...
The retro-ene reaction of 2-vinylcyclohexanols occurs readily
in the vapor phase at 400-450° producing unsaturated carbonyl
compounds in good yields. The starting- materials were prepared in
general by the carbenoid addition reaction of ethyl diazoacetate,
appropriately substituted cyclohexene, and copper catalyst to
produce bicyclic esters which were reduced to the...
During a study of the abnormal dienone-phenol rearrangement
discovered by Marvell and Geiszler, Imel (1960) found that 4-oxo-3,3-dimethyl-3,4-dihydrophenanthrene rearranged slowly to a phenol
which was tentatively identified as 3,4-dimethyl-l-phenanthrol;
further evidence to support this assignment was deemed essential.
The recent work by Mallory on the photochemical conversion of
stilbenes to...
The familiar equilibrium between 1, 7- octadiene and cyclooctene
at temperatures exceeding 3000, indicates that an ene-retroene
process could be used as a six atom ring expansion method. To test
this possibility we prepared both cis and trans isomers of 1, 2- diallyl-
1, 2 -bis (trimethylsiloxy) cyclohexane and pyrolyzed...
Bicyclo [6.1.0] non-4-ene was prepared by two routes; (1) reaction
of cis-cis-1, 5-cycloöctadiene with methylene iodide and zinc-copper
couple, (2) sodium-methanol reduction of 9, 9-dibromobicyclo-[6.1.0] non-4-ene. The bicyclononene was characterized by its infrared
spectrum, nuclear magnetic resonance spectrum and common
physical properties. The olefin was hydrogenated to bicyclo [6.1.0] -...
The preparation of 4-(3-hydroxypropyl) cyclohexanone and
of 4-(3-hydroxypropyl) cyclohexene and a number of their derivatives
as potential precursors of asymmetrically substituted bicyclo [3, 3, 1]
nonanes is described.
The ketone, 4-(3-hydroxypropyl) cyclohexanone, was prepared
from p-allylanisole by three different routes. Common to each
route was an initial hydroboration-oxidation followed by...
An improved procedure for the preparation of β-(3-cyclohexenyl) propionic acid from 4-vinylcyclohexene was developed. The
Friedel-Crafts cyclization of β-(3-(3-cyclohexenyl) propionyl chloride
with aluminum chloride was shown to give one bicyclic chlorine
containing ketone in 41% yield. This ketone was identified by a combination of spectral and chemical methods as a...
PART I. A chemical examination of the materials toxic to fish in
kraft pulp mill wastes has been made as part of a water pollution
study. Thirty gallons of "foul condensate" from a typical kraft mill
gave 14 g of organic material when extracted with methylene chloride,
and an additional...