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1, 2, 4 - triazole-aldehydes.

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Browne, Elaine Joy(Engels) (1961) 1, 2, 4 - triazole-aldehydes. PhD thesis, University of Tasmania.

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Abstract

Althouth many C-aldehydes of azoles and azines, including
those of 1,2,3-triazoles, are known and readily obtainable,
free aldehydes derived from 1,2,4-triazolo do not appear to
have been isolated previously. The main aim of the work submitted
in this thesis was the synthesis of such 1,2,4-triazoleC-aldehydes.

Frerichs and Beckurts (26) isolated the phenylhydrazone of
1-phenyl-5-hydroxy-1,2,4-triazole-3-aldenyde from the complex
mixture produced by reaction of phenylhydrazine with chloroacetylurethane
or chloroacetylurea, but did not prepare the
aldehyde itself. Parkes (58) prepared the 2 0 4,-dinitro-phenylhydrazone
of 0 (or N)-acetyl-3-hydroxy-1,2,4-triazole-5-aldehyde. The
crude free aldehyde was formed by ozonolysis of the
corresponding 5-styryl compound, followed by treatment with
Adams'catalyst but it could not be obtained pure.
Apart from these cases, 1,2,4-triazole-C-a1dehydes or their
derivatives have not been noted in the literature.
The chemistry of the 1,2,4-triazoles has recently been
reviewed (66), but relatively little is known when compared
with the chemistry of other i-heteroarumatic series. A preliminary
study of the properties of the 1,2 0 4-triazoles
suggested that the aldehydes might not be prepared as readily
as in some other series.
A brief summary is therefore given of the types of reaction
which 1,2,4-triazoles might be expected to undergo, with
reference to what is known of the electron distribution in
the nucleus. This is compared with observed reactivity, or otherwise,in the few specific cases which have been described or studied. From this, limitations imposed by the
intrinsic properties of the nucleus could be taken into
account, to to some extent ,in seeking the course of reaction
most likely to yield the desired compounds. Unfortunately,
Levi quantitative measurements are available. Several
1,2,4-triazole-aldehydes have been obtained and observations
made of the properties of the 1,2,4-triazoles during; the
course of this work, do, in general agree with what was expected.

Item Type: Thesis (PhD)
Keywords: Aldehydes
Copyright Holders: The Author
Additional Information:

Thesis (Ph.D) - University of Tasmania, 1962. Reprint from Chemistry and industry, 1960, pp. 1085-86 incl. at end of text

Date Deposited: 25 Nov 2014 00:41
Last Modified: 11 Mar 2016 05:56
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