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The first direct fabrication of A2B- and A3-type B(III)subchlorins from meso-ethoxycarbonyl-substituted tripyrrane has been realized by condensation with appropriate acid chlorides (benzoyl chloride, butyryl chloride, and ethyl chlorooxoacetate). The aliphatic acid chloride-based annulation reaction is new to subporphyrinoid chemistry. The phenyl (6a)- or n-propyl (6b)-substituted derivatives could be oxidized to the corresponding B(III)subporphyrins upon refluxing with DDQ, whereas the triethoxycarbonyl moiety (6c) was found to be resistant to oxidation and exhibits the most red-shifted absorption (587 nm) and emission (604 nm). The study indicates that absorption and emission behaviors of the B(III)subchlorin can be tuned by the introduction of electron-rich or electron-deficient substituents at the meso-position. B(III)subchlorins 6a and 6c generate singlet oxygen efficiently (44 and 40%, respectively) and, thus, may find application as potential photosensitizers in photodynamic therapy (PDT).

A mild and efficient method for the synthesis of organic peroxyesters from acid chlorides and tertiary alkyl hydroperoxides in the presence of aqueous solution of inorganic base is described. The process was conducted in a tri-liquid system using quaternary onium salts and polyethylene glycols as phase-transfer catalysts. A model reaction of cumyl hydroperoxide (CHP) with butyryl chloride was investigated under a wide range of conditions. Selected peroxyesters were obtained in moderate to high yields (62–93%).

In this study, we discovered and isolated an attractant for a mealybug-parasitic wasp Anagyrussawadai from an esterification product prepared with commercialized lavandulol (2-isopropenyl-5-methyl-4-hexen-1-ol) and butyryl chloride. Using gas chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance spectroscopy, we determined the structure of the compound to be (2,4,4-trimethyl-2-cyclohexenyl)methyl butyrate (cyclolavandulyl butyrate). This is a novel compound as far as we know, although the alcohol moiety has been known as a cyclization product from lavandulol. Cyclolavandulyl butyrate has two enantiomers, and the (−)-isomer, which is suggested to have S configuration, showed higher attractiveness. A potential use for the A. sawadai attractant for mealybug management in agricultural fields is discussed.

In the research described below, we have developed a convenient and effective method of synthesis of organic peroxyesters to achieve 60–98% yields under extreme mild conditions. The study has been conducted on a model system using a reaction of acylation of 1-methyl-1-phenylethyl hydroperoxide (CHP) by means of butyryl chloride in the presence of solid Na2CO3 and being performed under conditions of phase transfer catalysis (PTC). The effect of the following parameters on the reaction was tested: temperature, Na2CO3 amount, catalyst structure and solvent polarity.

The acylation of thiophene by butyryl chloride has been studied in the liquid phase in the presence of 12 catalysts: HZSM-5, H-mordenite, and HY (ultrastable Y) with various framework Si/Al ratios, various numbers of Bronsted and Lewis sites, and various amounts of nonframework aluminum. The numbers of Bronsted and Lewis acid sites were obtained by FT-IR using chemisorbed ammonia, as described elsewhere. There is a correlation between the initial rates of reaction and the number of Lewis acid sites, whereas there is no correlation between the initial rates and the number of Bronsted sites. The correlation with the number of Lewis sites may be considered significant, since it expands on more than one order of magnitude. Poisoning of the catalyst probably results from the oligomerization on butyryl chloride. No carboxylic acid has been detected in the course of the reaction. No attempt has been made to determine the nature of the poisoning reaction.

The treatment of succinic acid with lauroyl or stearoyl chloride gave the five-membered β-diketone (II) substituted with a long chain at the α-position, together with a trimer (III) of the acyl chloride. Bicyclo[3.3.1]nonane-2, 4-dione (VI) substituted with a methyl or ethyl group at the C3-position was prepared from cyclohexane-1, 3-dicarboxylic acid (V) and propionyl or butyryl chloride, respectively. D-Camphoric acid afforded an unexpected product, 4-acyl-2, 2, 3-trimethyl-3-cyclopentenecarboxylic acid (IX), on reaction with acyl chloride. Although acetyl chloride gave no product on treatment with succinic acid, it afforded 3-acetylbicyclo[3.2.1]octane-2, 4-dione (XI), 3-acetylbicyclo[3.3.1]nonane-2, 4-dione (VId), and 2-acetylcyclohexane-1, 3-dione (XII) on reaction with the corresponding dicarboxylic acids.

We describe a procedure for treatment of thin-layer chromatographic serum lipid patterns so that they may be stained by dyes for evaluation by densitometry. After development of the chromatogram [Clin. Chem. 18, 384 (1972)] the plates are dried and sprayed with butyryl chloride. This esterifies the free cholesterol. After drying, the plate is treated with iodine monobromide, to add iodline to the double bonds. The triacylglycerols (triglycerides), cholesterol esters, free cholesterol, and phospholipids are now all in the form of esters with no unsaturated double bonds. The free fatty acids are also now saturated. The chromatogram is now stained with basic fuchsine in acetate buffer (0.1 mol/liter, pH 5.0). Excess stain is removed with a buffered solution of guanidine hydrochloride. Erythrosine B may also be used. With basic fuchsine the background will be a uniform pink. With erythrosine B the background is white, but the stain tends to be washed out of the free fatty acids. The chromatograms are evaluated by densitometry, with use of a 540-nm filter for basic fuchsine and a 520-nm filter for erythrosine B. The stained chromatograms and densitometric scans accurately represent the relative concentration of the various lipid fractions as compared to that of an internal standard, and correlate with the nature of the disease being explored.

Properties of fluorine-adsorbed active carbon (FAAC), expected to be a new fluorinating agent, were investigated by means of TG, X-ray diffraction, and ESCA. The fluorine in FAAC was desorbed by heat treatment in a vacuum at temperatures higher than 200 °C. The X-ray diffraction and ESCA measurements suggest that fluorine is inserted between the carbon layer planes of the active carbon, and combines with carbon atoms weakly in comparison with the C–F covalent bond. The reactivity of FAAC against several organic compounds was studied. 1-Butanol, 1-butanethiol, and cyclohexylamine were oxidized. Butyryl chloride was fluorinated to give butyryl fluoride.