1-(2-pyridyl)-3-methyl-3-butene-2-ol was prepared by allowing 2-picolyllithium to react with methacrolein.
In the reaction of picolyllithium with crotonaldehyde, two products 1-(2-pyridyl)-4-methyl-3-butene-2-ol and 1-(2-pyridyl)-4-methyl-2-butene-4-ol were formed.
1-(2-pyridyl)-3-methyl-3-butene-2-ol was subjected to the low
pressure hydrogenation, using methanol as solvent and PtO₂ as catalyst. A red yellow liquid 1-(2-pyridyl)-3-methyl-2-butanol was
obtained. Derivatives of the...
The reaction of certain purin-8-ols with phosphorus
oxychloride and N,N-diethylaniline are described.
9-Amino-6-chloropurin-8-ol monohydrate reacted with
phosphorus oxychloride and N, N-diethylaniline to yield
the phosphorus oxychloride adduct. Other purin-8-ols
were prepared and the production of analogs similar to
the previously mentioned adduct was attempted.
6-Chloropurin-8-ol and 6, 9-diaminopurin-8-ol hydrochloride
monohydrate...
Both oxy-Cope and siloxy-Cope rearrangements involve
(1, 3) and (3, 3) sigrnatropic shifts. Both the concerted mechanism,
and the stepwise mechanism via a diradical intermediate are possible.
In a cyclic system such as cis-l-vinylcyclooct-3-en-l-ol, the thermal
rearrangement takes place preferably through a diradical intermediate.
At high temperature, the reaction also...
The thermolysis of trans-1 -trimethylsiloxy- 1-vinylcyclotridec-
3-ene (VI-OTMS) led to the formation of two major products: 4-vinylcyclotridecanone
(VII) and cyclopentadec-5-en-l-one (VIII) after
hydrolysis. Ketone VII is produced by a concerted [3, 3] sigmatropic
shift, while ketone VIII is formed by a [1, 3] sigmatropic shift with
a concerted or diradical...
The thermal and anionic rearrangements of substituted 1-vinyltrans-
cyclotridec-3-en-l-ol compounds have been studied to determine
what effects substituents would have on the sigmatropic shift when
placed on the two positions of the 1-vinyl group.
For the thermal rearrangements, the a-substituted vinyl-trans-cyclotridecenols
gave both the [3,3] and [1,3] shift products of...
Examination of a proposed reaction scheme to prepare bicyclo-(2.2.0)hexan-1-ol produced the first known condensation of an
enamine with its carbonyl precursor. Hydrolysis of the resulting
dienamine gave an unusual conjugated cyclobutenone in which the
double bond is exocyclic. Characterization and reactions of the
cyclobutenone were successfully carried out.
The potassium salts of certain 1-vinylcycloalk-3-en-l-ols have
been found to undergo sigmatropic ring expansion rearrangements in
HMPA. Preliminary investigations of several benzo-substituted medium
ring systems were undertaken in order to determine which of these
was best suited for further study. A synthetic sequence leading to
the formation of 5-methy1-6-viny1-7,8,9,10-tetrahydro-6-benzocyclo-octenol,
which...
The purpose of this project was to study the reactions of 1-(α-pyridyl)-3-buten-1-ol (compound I) and to determine whether or
not the products of some of its reactions are quinolizinium salts.
Reaction of compound I with bromine or iodine yields halide
salts (when no external cooling is applied) instead of the...