By Jiro Tsuji (auth.)
Around 30 years in the past the transition steel chemistry bought nice impulses. within the concentration were reactions of nickel and cobalt and herein particularly their carbonyls. additionally business procedures were built. whilst the technical oxidation of ethylene with palladium chloride have been came upon, and a good quantity oflaboratory reactions, many teams have became in the direction of this topic. except very important business procedures - acetaldehyde and vinylacetate from ethylene - various conversions and catalytic reactions with palladium compounds were researched. Their mechanisms were cleared up and feature con tributed to a greater figuring out of the complicated chemistry of palladium. final yet no longer least those reactions have additionally served for extra figuring out of natural transition steel compounds and catalyses more often than not. various traditional reactions look this day in a unique mild. the results of co-
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Extra info for Organic Synthesis with Palladium Compounds
Sample text
Pd 2+ CH 2 =CHCH 3 + AcOH + O2 -----+ CH 2 =CHCH 2 0Ac Cu 2+ Methallyl acetate and 2-methylene-l ,3-diacetoxypropane were formed in good yields by gas phase oxidation of isobutylene with a palladium catalyst supported on alumina [156]. Allylic acetoxylation and coupling reactions were effected by oxidation of isobutylene and methylenecycloalkanes with Pd(OAch [157]. Palladium catalyzed synthesis of glycol derivatives by the nucleophilic addition reaction to ethylene in acetic acid was discovered by several companies as a promising industrial process for ethylene glycol production [58, 158-160].
P_dC_I_zCC_H_3C_N_>Z_/T_HF__ NH2 2. Et~ 0-l ~NAcH H 3 2,2-Dimethyl-l ,2-dihydroquinoline was obtained from 2-(3,3-dimethylallyl)aniline. 3-Methyl-I,2,3,4-tetrahydroisoquinoline was formed from 2-allylbenzylamine. 33 Oxidation Reactions with Pd 2+ Compounds As a related reaction, 2-pyridones were obtained by the oxidative cyclization of 2,4-alkadienamide with PdC1 2 [261]. o RCH=CHCH=CHCONH 2 RAw~o I H Similarly, hydrazides of a, /3-unsaturated acids were cyclized to form 3-pyrazolones [262]. 35-42% Even urea derivatives of unsaturated acids can be cyclized with PdCl2 .
Reactions of other nuc1eopbiles with substituted 1T-allyl complexes were carried out in THF, or DMF at room temperature in the presence of an excess of PPh3, or PBU3 [352,353]. Synthetic application of the reaction of active methylene compounds with 1T-allyl complexes formed from various olefins by the reaction 3-b-ii has been explored as a method of introducing functional groups at allylic positions of olefins via 1T-allyl complex formation [295,301,352-357]. A considerable, but not complete regioselectivity was observed in the complex formation from substituted olefins [303].