The catalytic decarbonylation reaction of aliphatic carboxylic acids can be carried out in the presence of an iron complex, and it proceeds smoothly to give α-olefins with high selectivity.

ChemInformVolume 43, Issue 26 Preparative Organic Chemistry ChemInform Abstract: Iron-Catalyzed Decarbonylation Reaction of Aliphatic Carboxylic Acids Leading to α-Olefins. Shinji Maetani, Shinji Maetani Dep. Chem., Grad. Sch. Sci., Osaka Prefect. Univ., Osaka 599, JapanSearch for more papers by this authorTakahide Fukuyama, Takahide Fukuyama Dep. Chem., Grad. Sch. Sci., Osaka Prefect. Univ., Osaka 599, JapanSearch for more papers by this authorNobuyoshi Suzuki, Nobuyoshi Suzuki Dep. Chem., Grad. Sch. Sci., Osaka Prefect. Univ., Osaka 599, JapanSearch for more papers by this authorDaisuke Ishihara, Daisuke Ishihara Dep. Chem., Grad. Sch. Sci., Osaka Prefect. Univ., Osaka 599, JapanSearch for more papers by this authorIlhyong Ryu, Ilhyong Ryu Dep. Chem., Grad. Sch. Sci., Osaka Prefect. Univ., Osaka 599, JapanSearch for more papers by this author Shinji Maetani, Shinji Maetani Dep. Chem., Grad. Sch. Sci., Osaka Prefect. Univ., Osaka 599, JapanSearch for more papers by this authorTakahide Fukuyama, Takahide Fukuyama Dep. Chem., Grad. Sch. Sci., Osaka Prefect. Univ., Osaka 599, JapanSearch for more papers by this authorNobuyoshi Suzuki, Nobuyoshi Suzuki Dep. Chem., Grad. Sch. Sci., Osaka Prefect. Univ., Osaka 599, JapanSearch for more papers by this authorDaisuke Ishihara, Daisuke Ishihara Dep. Chem., Grad. Sch. Sci., Osaka Prefect. Univ., Osaka 599, JapanSearch for more papers by this authorIlhyong Ryu, Ilhyong Ryu Dep. Chem., Grad. Sch. Sci., Osaka Prefect. Univ., Osaka 599, JapanSearch for more papers by this author First published: 31 May 2012 https://doi.org/10.1002/chin.201226052Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume43, Issue26June 26, 2012 RelatedInformation

Vaska's complex, IrCl(CO)(PPh(3))(2), when combined with KI as an additive, served as an excellent catalyst for the decarbonylation of long-chain aliphatic carboxylic acids to give internal alkenes with high selectivity. On combination with KI and Ac(2)O as additives under controlled temperatures, decarbonylation proceeded to give terminal alkenes with high selectivity.

A direct method for the photocatalytic in situ generation of HBr from bromine and isooctane and subsequent photocatalyzed regioselective addition is presented.

A triphasic phase-vanishing (PV) system comprised of an alkane, perfluorohexanes, and bromine was successfully combined by photoirradiation to efficiently generate hydrogen bromide, which underwent radical addition with 1-alkenes in the hydrocarbon layer to afford terminal bromides in high yields.

A triphasic phase-vanishing (PV) system comprised of an alkane, perfluorohexanes, and bromine was successfully combined by photoirradiation to efficiently generate hydrogen bromide, which underwent radical addition with 1-alkenes in the hydrocarbon layer to afford terminal bromides in high yields.

The N-hydroxyphthalimide derivatives, F(15)- and F(17)-NHPI, bearing a long fluorinated alkyl chain, were prepared and their catalytic performances were compared with that of the parent compound, N-hydroxyphthalimide (NHPI). The oxidation of cyclohexane under 10 atm of air in the presence of fluorinated F(15)- or F(17)-NHPI, cobalt diacetate [Co(OAc)(2)], and manganese diacetate [Mn(OAC)(2)] without any solvent at 100 degrees C afforded a mixture of cyclohexanol and cyclohexanone (K/A oil) as major products along with a small amount of adipic acid. It was found that F(15)- and F(17)-NHPI exhibit higher catalytic activity than NHPI for the oxidation of cyclohexane without a solvent. However, for the oxidation in acetic acid all of these catalysts afforded adipic acid as a major product in good yield and the catalytic activity of NHPI in acetic acid was almost the same as those of F(15)- and F(17)-NHPI. The oxidation by F(15)- and F(17)-NHPI catalysts in trifluorotoluene afforded K/A oil in high selectivity with little formation of adipic acid, while NHPI was a poor catalyst under these conditions, forming K/A oil as well as adipic acid in very low yields. The oxidation in trifluorotoluene by F(15)- and F(17)-NHPI catalysts was considerably accelerated by the addition of a small amount of zirconium(IV) acetylacetonate [Zr(acac)(4)] to the present catalytic system to afford selectively K/A oil, but no such effect was observed in the NHPI-catalyzed oxidation in trifluorotoluene.