Summary
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1.
Two methods were developed for the synthesis of the previously unknown alkenyl 2-chlorovinyl ketones. The first method consists in the condensation of acid chlorides, of α,β-unsaturated acids with acetylene in presence of aluminum chloride.The second method consists in the condensation of acid chlorides of a- and β-chloro acids with acetylene in presence of aluminum chloride and subsequent treatment of the reaction product with diethylaniline.
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2.
It was shown that alkenyl 2-chlorovinyl ketones react with 2-naphthol in presence of ferric chloride with formation of 3-(1-alkenyl)naphtho[2,1-b]pyrilium chloroferrates. This indicates the high mobility of chlorine in the alkenyl 2-chlorovinyl ketone molecule and proves the structure of these compounds.
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Literature cited
N. Kochetkov, Prog. Chem. 24, 32 (1955).
A. N. Nesmeyanov, N. K. Kochetkov, and M. I. Rybinskaya, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1950, 350.
N. K. Kochetkov, A. Ya. Khorlin, and M. Ya. Karpeisky, J. Gen. Chem. 26, 595 (1956) (T.p. 643).
N. K. Kochetkov. A. N. Nesmeyanov, and N.. A. Semenov, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1952, 8' (T. p. 9 ) '
N. K. Kochetkov, Prac. Acad. Sci. USSR 82,593 (1952).
M. Kharash, H. Herbert and C. Brown. J. Am. Chem. Soc. 62, 925 (1940).
H. Wieland and L. Bettag, Ber. 55, 2246 (1922).
A. Ya. Yakubovich and E. N. Merkulova, J. Gen. Chem. 16,55 (1946).
A. N. Nesmeyanov, N. K. Kochetkov, and M. I. Rybinskayal, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1953. 479 (T.p. 429).'
L. Smith and V. Engelhardt, J. Am. Chem. Soc. 71, 2671 (1949).