The reaction of 2-chloroquinoline with the sodium salts of t-butyl cyanoacetate, ethyl cyanoacetate, and malononitrile gives t-butyl cyano-2( lH)-quinolylideneacetate ( 1 ), ethyl cyano-2( 1H)-quinolylidene acetate (2)) and 2( 1H)-quinolylidenemalonitrile (3), respectively. The structures assigned to these compounds are based upon infrared, ultraviolet, and n.m.r. spectroscopy. The reaction of 2-chloro-l,10-phenanthroline with t-butyl cyanoacetate yields t-butyl cyano-2-( lH)-l,l0-phenanthrolylideneacetate (4). 2-Chloroquinoline reacts in an "abnormal" manner with cyanoacetamide to give 2-quinolyl-2( 1H)-quinolylideneacetonitrile (8). The reactions of the esters 1 , 2 , and 4 with acid were studied.We have found that 2-chloroquinoline reacts smoothly with the sodium salts of t-butyl cyanoacetate, ethyl cyanoacetate, and malononitrile to give t-butyl cyano-2(1H)-quinolylideneacetate (1)) ethyl cyano-2(1H)quinolylideneacetate (2), and 2( lH)-quinolylidenemalononitrile (3), respectively. Similarly, the reaction between 2-chloro-1, 10-phenanthroline and the sodium salt of t-butyl cyanoacetate gives t-butyl cyano-2(lH)-1, 10-phenanthrolylideneacetate (4).
COMMUNICATIONSfigurations of the 2-butyl carbon atom and phosphorus atom in (-)-0-2-butyl S-2-(ethylthio)ethyl (-)-ethylphosphonothioate (la) and (-)-0-2-butyl S-2-(dimethylammonium)ethyl (-) -ethylphosphonothioate hydrogen oxalate (2a) also are assigned the configurations RcSp. The configurations of the remaining chiral isomers may be deduced from their respective optical rotations.
A method is presented for the determination of the plant growth regulator maleic hydrazide (MH; l,2-dihydro-3,6-pyridazinedione) in tobacco and tobacco smoke. Residues are converted to the bis(trimethylsilyl) derivative before analysis by gas-liquid chromatography. The method has been applied to cigarettes and condensed smoke and has been used to determine the per cent transfer of MH into cigarette smoke. Free MH residues could be determined directly on the tobacco samples, whereas total MH values were obtainable only after acid hydrolysis. In spite of large MH residues in tobacco, only 0.2% of the MH was transferred into smoke.
The fate and stability of maleic hydrazide (MH) applied to Burley Tobacco and soil was examined. Four dosages of MH, from one-tenth to twice the recommended amount, were applied to tobacco at various stages of maturity. Residual quantities of MH in green and cured plants, as well as in soil, were determined by our derivatization-gas chromatography method. The effects of different application rates
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