The Art of Writing Reasonable Organic Reaction Mechanisms

By Robert B. Grossman

Intended for college students of intermediate natural chemistry, this article exhibits how you can write an inexpensive mechanism for an natural chemical transformation. The dialogue is prepared via forms of mechanisms and the stipulations less than which the response is carried out, instead of via the general response as is the case in such a lot textbooks. every one bankruptcy discusses universal mechanistic pathways and indicates functional information for drawing them. labored difficulties are incorporated within the dialogue of every mechanism, and "common mistakes indicators" are scattered through the textual content to warn readers approximately pitfalls and misconceptions that bedevil scholars. each one bankruptcy is capped by means of a wide challenge set.

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283 . . . . . . . 286 3879_efm1_pi-xvi 10/22/02 9:57 AM web page xvi xvi Contents 6. 2. three 6. 2. four 6. 2. five Hydrozirconation (Zr) . . . . . . . . . . . . . . . . Alkene Polymerization (Ti, Zr, Sc, and others) . . . Cyclopropanation, Epoxidation, and Aziridination of Alkenes (Cu, Rh, Mn, Ti) . . . . . . . . . . . . 6. 2. 6 Dihydroxylation and Aminohydroxylation of Alkenes (Os) . . . . . . . . . . . . . . . . . . . . . 6. 2. 7 Nucleophilic Addition to Alkenes and Alkynes (Hg, Pd) . . . . . . . . . . . . . . . . . . . . . . . 6. 2. eight Conjugate Addition Reactions (Cu) . . . . . . . . . 6. 2. nine Reductive Coupling Reactions (Ti, Zr) . . . . . . . 6. 2. 10 Pauson–Khand response (Co) . . . . . . . . . . . . 6. 2. eleven Dötz response (Cr) . . . . . . . . . . . . . . . . . . 6. 2. 12 Metal-Catalyzed Cycloaddition and Cyclotrimerization (Co, Ni, Rh) . . . . . . . . . . . 6. three Substitution Reactions . . . . . . . . . . . . . . . . . . . . 6. three. 1 Hydrogenolysis (Pd) . . . . . . . . . . . . . . . . . 6. three. 2 Carbonylation of Alkyl Halides (Pd, Rh) . . . . . . 6. three. three Heck response (Pd) . . . . . . . . . . . . . . . . . 6. three. four Coupling Reactions among Nucleophiles and C(sp2) –X: Kumada, Stille, Suzuki, Negishi, Buchwald–Hartwig, Sonogashira, and Ullmann Reactions (Ni, Pd, Cu) . . . . . . . . . . . . . . . . 6. three. five Allylic Substitution (Pd) . . . . . . . . . . . . . . . 6. three. 6 Pd-Catalyzed Nucleophilic Substitution of Alkenes; Wacker Oxidation . . . . . . . . . . . . . . . . . . 6. three. 7 Tebbe response (Ti) . . . . . . . . . . . . . . . . . 6. three. eight Propargyl Substitution in Co–Alkyne Complexes . 6. four Rearrangement Reactions . . . . . . . . . . . . . . . . . . . 6. four. 1 Alkene Isomerization (Rh) . . . . . . . . . . . . . 6. four. 2 Olefin and Alkyne Metathesis (Ru, W, Mo, Ti) . . 6. five removing Reactions . . . . . . . . . . . . . . . . . . . . . 6. five. 1 Oxidation of Alcohols (Cr, Ru) . . . . . . . . . . . 6. five. 2 Decarbonylation of Aldehydes (Rh) . . . . . . . . . 6. 6 precis . . . . . . . . . . . . . . . . . . . . . . . . . . . difficulties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 287 . . 288 . . 290 . . 292 . . . . . . . . . . 294 297 297 301 303 . . . . . . . . . . 306 309 309 311 313 . . 314 . . 318 . . . . . . . . . . . . . . . . . . . . . . 319 321 322 323 323 323 326 326 326 327 328 7 Mixed-Mechanism difficulties 334 a last notice 339 Index 341 3879_a01_p1-49 10/22/02 9:58 AM web page 1 1 the fundamentals 1. 1 constitution and balance of natural Compounds If technology is a language that's used to explain the universe, then Lewis constructions— the sticks, dots, and letters which are used to symbolize natural compounds—are the vocabulary of natural chemistry, and response mechanisms are the tales which are advised with that vocabulary. as with every language, it will be significant to profit find out how to use the natural chemistry vocabulary safely to be able to speak one’s principles. the foundations of the language of natural chemistry occasionally appear capricious or arbitrary; for instance, you'll locate it obscure why RCO2Ph is shorthand for a constitution with one terminal O atom, while RSO2Ph is shorthand for a constitution with terminal O atoms, or why it's so very important that ǟ Ǟ and never L be used to point resonance. yet natural chemistry isn't any diversified during this approach from languages akin to English, French, or chinese language, which all have their very own capricious and arbitrary ideas, too. (Have you ever puzzled why I, you, we, and so they stroll, yet she or he walks?

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