DeShong, Philip published the artcileIntermolecular and intramolecular azomethine ylide [3 + 2] dipolar cycloadditions for the synthesis of highly functionalized pyrroles and pyrrolidines, Safety of 2,3-Dibromopropionylchloride, the publication is Journal of Organic Chemistry (1985), 50(13), 2309-15, database is CAplus.
N-Alkyl and N-arylaziridines carrying a single carboxy ester function, e.g., I, undergo thermally induced electrocyclic ring opening to produce azomethine ylides, which subsequently react with acetylenes or olefins to yield substituted pyrroles, e.g., II, or pyrrolidines, e.g., III, resp. The [3 + 2] dipolar cycloaddition reaction can be performed in either an intermol. or intramol. mode and displays high regioselectivity and stereoselectivity with a variety of dipolarophiles. The yield of cycloadducts depends on the electronic characteristics and the substitution pattern of the dipolarophile, and on the mode of cycloaddition employed. In the intermol. reaction, the yield of adducts is poor unless the dipolarophile is activated. Intramol. cycloadditions with monosubstituted olefins or acetylenes give adducts in yields of 45-70%. Although the yields of adducts in these instances are moderate, the starting materials are readily prepared and the method is an effective means for the assembly of a structurally complex heterocyclic system with high regiochem. and stereochem. control of peripheral substituents. When the dipolarophilic component is disubstituted, the cycloaddition gives synthetically useful yields if the dipolarophile carries an electron-withdrawing functionality.
Journal of Organic Chemistry published new progress about 18791-02-1. 18791-02-1 belongs to chlorides-buliding-blocks, auxiliary class Aliphatic Chain, name is 2,3-Dibromopropionylchloride, and the molecular formula is C3H3Br2ClO, Safety of 2,3-Dibromopropionylchloride.
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