Site-selective nucleophilic ring-opening reactions of 2-arylazetidine-2-carboxylic acid ester-derived tetraalkyl ammonium salts 2 with tetrabutylammonium halides (BuNX) to give tertiary alkyl halides are successfully demonstrated. For example, a nucleophilic ring-opening reaction of 2-(-tolyl) derivative 2a with 1.2 equivalents of tetrabutylammonium fluoride (BuNF) in THF at 60 °C preferentially proceeded at a more substituted carbon atom (2-position) compared to a less-substituted carbon atom (4-position) and afforded -butyl 4-(dimethylamino)-2-fluoro-2-(-tolyl)butanoate 3aa in 71% yield as the corresponding tertiary alkyl fluoride.
View Article and Find Full Text PDFIn order to fully understand the role of volatile organic compounds (VOCs) under natural conditions, an adaptable analytical method was developed as the first step. beta-Ionone, beta-cyclocitral, 2-methyl-1-butanol and 3-methyl-1-butanol were simultaneously analyzed in addition to geosmin and 2-MIB using GC/MS with SPME. The slight modification of a known method allowed the simultaneous detection and quantification of these VOCs.
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