NOTES 1671 trichloride (3.76 g., 0.032 mole) in 20 ml. of methylene chloride at -80°. After allowing the mixture to warm, the solvent was removed at the pump. The yellow-orange solid residue was recrystallized from benzene and then from carbon disulfide. Infrared analysis indicated that the compound was triphenylchloromethane. This was confirmed by hydrolyzing a weighed sample in aqueous acetone and titrating the hydrochloric acid liberated.
Ethyl atrópate, CH^CCCeHsjCOOCaHs, underwent conjugate addition with phenylmagnesium bromide and with alkali diand triphenylmethides to form corresponding /3-substituted products. Ethyl atrópate also underwent conjugate additions with the 1,2-dialkali salts of benzophenone and benzophenone anil to afford a lactone and a -amino ester, respectively. Several new /3-amino esters were prepared by similarly condensing ethyl atrópate with certain alkali amides or with appropriate free amines. Various alkylations of intermediate carbanions were effected to afford «-substituted derivatives. Some related reactions were also realized.
A semiquantitative study was made of the two possible modes of alkaline cleavage of the 2-acetyl derivatives of cyclopentanone, cyclohexanone, cycloheptanone, and cyclooctanone. 2-Acetylcyclopentanone underwent largely ring opening and 2-acetylcyclohexanone, mainly ring opening. However, only side chain cleavage was realized with 2-acetylcycloheptanone and 2-acetylcycloóctanone, Also, only side chain cleavage was observed with 2-benzoylcycloheptanone and 2-benzoylcyclooctanone. The 2-methyl derivatives of 2-acetylcyclopentanone and 2-acetylcyclohexanone underwent relatively less ring opening than the corresponding unsubstituted 2-acetylcyclanones. The boron fluoride-acid anhydride and the sodium amideacid chloride methods of acylation of ketones were extended to cycloheptanone and cyclooctanone.
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