“…All compounds were fully characterized by NMR, IR, and mass spectra. 2,2-Dimethyl-4-decene ( 4d ), 6-tetradecene ( 4e ), 1-phenyl-2-octene ( 4f ), and 1-phenyl-1-heptene ( 4i ) had physical data identical to that reported in the literature. 3-Nonene ( 4a ), 1-nonene ( 4g ), and allylbenzene ( 4h ) were recognized by comparison with commercial samples (Aldrich).…”
“…However, an increase in the reaction temperature above 100°C might induce the decomposition of the substrate and therefore reduce the yield (Table 1, Entry 2). [17] To understand the catalytic process of this reaction, a kinetic isotope effect was investigated by using 2-deuteriobenzaldehyde O-methyloxime (1a-D) to react with 2a to form 3a and 3a-D (Scheme 1). in acetic acid at 80°C.…”
Section: Resultsmentioning
confidence: 99%
“…Unfortunately, almost no desired product was obtained when styrene was employed under the reaction conditions, because the acetoxylation of styrene occurred under the acidic conditions. [17] To understand the catalytic process of this reaction, a kinetic isotope effect was investigated by using 2-deuteriobenzaldehyde O-methyloxime (1a-D) to react with 2a to form 3a and 3a-D (Scheme 1). The k H /k D ratio was determined to be 0.96, [18] which indicated that the palladium(II)catalyzed C-H bond cleavage of benzaldehyde O-methyloxime (1a) does not occur in the rate-determining step.…”
Palladium(II)‐catalyzed ortho‐olefination of arylaldehyde O‐methyloximes by using O‐methyloxime as a directing group gave 2‐alkenylarylaldehyde O‐methyloximes in moderate to good yields. After various reaction parameters (catalyst, oxidant, solvent, and reaction temperature) were examined, the optimal conditions for the reaction were identified. 2‐Alkenylarylaldehydes could be obtained conveniently by hydrolysis of the coupling products. The kinetic isotope effect (kH/kD) for the C–H bond activation was provided, and the possible mechanism of the reaction was proposed.
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