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Synthesis 2002(15): 2220-2224
DOI: 10.1055/s-2002-34854
DOI: 10.1055/s-2002-34854
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Convenient Preparation of
4-Methyl- and 4-Phenylseleno-1,1,1-trihalo-3-
alken-2-ones
and their Usefulness in the Synthesis of 3-Trihalomethylisoselenazoles
Weitere Informationen
Received
28 February 2002
Publikationsdatum:
21. Oktober 2002 (online)
Publikationsverlauf
Publikationsdatum:
21. Oktober 2002 (online)
Abstract
A convenient synthesis of fourteen 4-methyl- and 4-phenylseleno-1,1,1-trihalo-3-alken-2-ones [CX3C(O)CH=CR1SeR, where X = F, Cl; R = Me, Ph; and R1 = H, alkyl, aryl] from the reaction of the corresponding 4-methoxy-1,1,1-trihalo-3-alken-2-ones with methyl- or phenylselenols in the presence of boron trifluoride etherate is reported. The reaction of 4-methylseleno-1,1,1-trihalo-3-alken-2-ones with bromine and ammonia lead to 3-trihalomethylisoselenazoles in good yields. The usefulness of the trichloromethyl group as a carboxyl group precursor was demonstrated by the conversion of 5-ethyl-3-trichloromethylisoselenazole to 5-ethyl-3-carboxyisoselenazole acid.
Key words
isoselenazoles - selenium - enones - halogens - heterocycles
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