serratosa - organic chemistry in action 2e (elsevier, 1996) ww

[...]... U 1,8-Diazabicyclo[5.4.0]undec-2-ene DCC Dicyclohexylcarbodiimide Diethyl tartrate DET DHP Dihydropyran D H Q Dihydroquinine D H Q D .Dihydroquinidine DlPT Diisopropyl tartrate DIBAL Diisobutyl aluminum hydride 1,4-bis(diphenylphosphino)DIOP 2,3-O-isopropylidene-2,3-hydroxybutane D M AP 4-Dimethylaminopyridine DME 1,2-Dimethoxyethane(glyme)... dihydroxylation ADP .Adenosine diphosphate AIB N .2,2'-Azobisisobutyronitrile AL Aldolase ATP .Adenosine triphosphate 9-BBN 9-Borabicyclo[3.3 llnonane BINAP .(2R,3S )-2 ,2'-Bis(diphenylphosphino )- '-binaphtyl 1,l BOM Benzyloxymethyl BSA Bovine serum albumin BTI Bis(thlocarbony1)imidazole Cp Cyclopentadienide anion DABCO 1,4-Diazabicycl0[2.2.2]octane... M E D m - C h o l o r o p e r b e n z o i c acid 2 - M e t h y l - 2 - e t h y l - 1,3-dioxolane MOM M O P Ms Methoxymethyl 2-Methoxy-2-propyl M e t h a n e s u l p h o n y l (Mesyl) M S NB S NMO N-Bromosuccinimide N-Methylmorpholine N-oxide PCC Pyridinium chlorochromate PDC ... philosophical point of view, although the word ~synthesis~ has a long tradition, it was Kant (172 5-1 804) who went deep into the modem meaning of the term, which, in turn, determined the chemical meaning presently accepted by all chemists Thus, in philosophy there is a difference between ~synthesis~ as a method -meaning the way of going from the simple to the complex- and ~synthesis~ as an operation -in which... reasoning, which is essentially intuitive and inductive and leads to genuine innovations This is to say, in contrast with analytical reasoning, synthetical reasoning implies an acquisition of new knowledge Using analytical reasoning what already exists can be deduced Nothing new comes from it: we only discover or unveil the mysteries and secrets of the world in which we live That was the precise meaning... Society offered, in 1850, a prize of 4.000 francs to any chemist who could prepare synthetic quinine in the laboratory In England, in 1856, only two years before Kekul6 and Couper laid the foundations of the structural theory, W.H Perkin [6], acting upon the advice of his mentor A.W Hofmann, attempted to synthesise quinine by the oxidative dimerization of allyltoluidine following the reaction: 2 C10H13N... exploratory processes of trial and error, leads finally to discovery In this context, we can say that organic synthesis is a heuristic activity In this book, rather than producing a textbook of organic chemistry, we hope to be able to show the science and art of organic chemistry in action 1.3 Pure substances Language: The Classical Structural Theory Chemistry is the science that deals with matter The... demonstrate things by logic, it is only through intuition that we discover new things In fact, as Poincar6 pointed out "logic only produces tautologies" In the same way that syllogisms and theorems are the essence of analytical reasoning, the "heuristic principles" are the essence of synthetical reasoning According to "The Oxford Dictionary", the word "heuristic" derives from the Greek heurisko ("I find")... natural dyestuffs alizarin and indigo, and, moreover, to open up the possibility of synthesising them It has been said that the development of organic chemistry in the last hundred years represents the most surprising application of a non-quantitative logical reasoning Even more surprising is that the structural theory of the organic chemists does not differ too much from the so-called graph theory 2_... activity In addition, only one enantiomer of quinine (1), the laevorotatory, corresponds to the natural compound and manifests the specific physiological properties associated with this substance OCH3 • quinine OCH3 2 quinidine Therefore, apart from the problem of linking all the carbon atoms of the carbon skeleton of tile molecule, every projected organic synthesis must also take into 2 See Appendix A- 1 . Studies in Organic Chemistry 51 ORGANIC CHEMISTRY IN ACTION The Design of Organic Synthesis SECOND EDITION This Page Intentionally Left Blank Studies in Organic Chemistry 51 ORGANIC CHEMISTRY. methods, products, instructions or ideas contained in the material herein. This book is printed on acid-free paper. Printed in The Netherlands Studies in Organic Chemistry Titles in this series:. edited by H. Dtirr and H. Bouas-Laurent 41 Organic Chemistry in Action. The Design of Organic Synthesis by F. Serratosa 42 Similarity Models in Organic Chemistry, Biochemistry and Related Fields