@article {1132, title = {Expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline}, journal = {Journal of Organic Chemistry}, volume = {70}, number = {26}, year = {2005}, note = {ISI Document Delivery No.: 995HBTimes Cited: 10Cited Reference Count: 38}, month = {Dec}, pages = {10872-10874}, type = {Article}, abstract = {The key compound responsible for the aroma of bread, 6-acetyl-1,2,3,4-tetrahydropyridine (1), has been constructed in an efficient three-step procedure from 2-piperidone in an overall yield of 56\%. Compound I was liberated in the final step under basic conditions. A related synthetic route produced 2-acetyl-1-pyrroline (2), the principal component of cooked rice, in 10\% overall yield.}, keywords = {BICYCLIC ENAMINES, BREAD FLAVOR COMPONENT, COOKED RICE, HYDROLYSIS, MECHANISM, MODEL SYSTEMS, POPCORN, QUANTITATIVE-ANALYSIS, ROAST-SMELLING ODORANTS, TERTIARY ENAMINES}, isbn = {0022-3263}, url = {://000234090300034}, author = {Harrison, T. J. and Dake, G. R.} } @article {3944, title = {Polyhaloporphyrins: Unusual ligands for metals and metal-catalyzed oxidations}, journal = {Accounts of Chemical Research}, volume = {30}, number = {6}, year = {1997}, note = {ISI Document Delivery No.: XE058Times Cited: 283Cited Reference Count: 63}, month = {Jun}, pages = {251-259}, type = {Review}, keywords = {halogenated porphyrins, HYDROGEN-PEROXIDE, HYDROXYLATION, Iron(III), IRON-PORPHYRIN COMPLEXES, manganese porphyrins, METALLOPORPHYRINS, MODEL SYSTEMS, porphyrins, SATURATED-HYDROCARBONS, TERT-BUTYL HYDROPEROXIDE}, isbn = {0001-4842}, url = {://A1997XE05800004}, author = {Dolphin, D. and Traylor, T. G. and Xie, L. Y.} } @article {3777, title = {A biomimetic study of cytochrome P450 related oxidations of toluenes using synthetic hemin}, journal = {Bulletin of the Chemical Society of Japan}, volume = {69}, number = {12}, year = {1996}, note = {ISI Document Delivery No.: WB844Times Cited: 6Cited Reference Count: 68}, month = {Dec}, pages = {3513-3521}, type = {Article}, abstract = {A mechanistic study of the oxidation of toluene and its derivatives in a model system designed to mimic cytochrome P450 (P450) using iron tetrakis(2,6-dichlorophenyl)porphyrin chloride (FeTPPC8Cl) and pentafluoroiodosylbenzene (PFIB:C(6)F(5)lO) in dichloromethane is reported. The oxidation products were the corresponding benzyl alcohols and aldehydes; no further oxidation products were observed. The relative reaction rates were obtained in competitive reactions including the use of deuterated analogues. In the present model system, Hammett plots and isotope effects indicated conclusively that the rate-determining step was a hydrogen atom abstraction to the oxoiron intermediate which was then followed by a rebound of an OH group. The concerted mechanism and the rebound mechanism were discussed in terms of the differences in reactivities between the model system and natural P450 enzymes and similar monooxygenation enzymes.}, keywords = {ALIPHATIC, AROMATIC-COMPOUNDS, CRYSTAL-STRUCTURE, DEPENDENT MONO-OXYGENASES, HYDROGEN-PEROXIDE, HYDROXYLATION, INDUCED, IRON(III) PORPHYRINS, LIVER MICROSOMAL CYTOCHROME-P-450, METABOLISM, MODEL SYSTEMS, RAT-LIVER}, isbn = {0009-2673}, url = {://A1996WB84400017}, author = {Nakano, T. and Agatsuma, N. and Kodama, S. and Kakuda, H. and Dolphin, D.} }