Advanced Problems in Organic Reaction Mechanisms - download pdf or read online

By McKillop

The Elsevier Tetrahedron natural Chemistry sequence is a topical sequence of monographs through world-renowned scientists in different fields of natural chemistry. The Tetrahedron natural Chemistry sequence has been very profitable in supplying a number of the best possible scholarly works in those topical components that experience confirmed to be of lasting caliber as vital reference assets. those books have supplied the working towards researcher, pupil and student with a useful resource of accomplished experiences in natural chemistry, predominantly within the components of synthesis and constitution decision, including:

* Reagents
* response mechanisms
* Molecular Diversity
* uneven Synthesis
* Multi-dimensional nmr
* Enzymatic Synthesis
* Organometallic Chemistry
* Biologically very important Molecules

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Me coc Me ocMe2 , N N / \ O 1 2 48. 2H 3 Propargylbenzotriazoles to Five-membered Heterocycles 1-Propargylbenzotriazole, readily available by alkylation of benzotriazole with propargyl bromide in the presence of sodium hydroxide, has been found to be a valuable building block for the synthesis of furans, dihydrofurans, pyrroles and indoles. The versatility of this type of chemistry for the synthesis of otherwise difficultly accessible heterocyclic systems is illustrated by the following typical transformations.

I 1 o 2 50. 3 Isoxazoles from Cyclopropanes Treatment of 2-aryl-l,l-dichlorocyclopropanes 1 under nitrating conditions with mixed acid at 0~ can give 3-aryl-5-chloroisoxazoles in yields of up to 85% depending on the nature of substituents in the aryl ring. The transformation is most efficient when the aromatic substituent is electron withdrawing (R = 4-NO2, 85%; R = 3-NO2, 31%; R = 2-NO2, 13%), but is very poor with electron donating groups (R = 4-Me, 2%; R = 4-MeO, only degradation products). Suggest a mechanism for isoxazole formation which accounts for these observations.

Give a mechanistic explanation for this transformation. O O ~ Me O R R R R 1 R = H, alkyl, vinyl 2 83. m-Terphenyls from Pyrones Alkali-catalysed reaction of the pyrones 1 with acetophenones ArlCOMe in DMF at room temperature results in smooth transformation into the m-terphenyls 2 (50-66%) and the pyranylideneacetates 3 (0-28%). Give mechanisms to account for the formation of 2 and 3 from 1. SMe SMe O2Me Ar Ar Ar~ ]~ CO -12Me Al Ar1 1 2 84. CO2Me 3 A Cascade Reaction Treatment of the readily accessible ester 1 with either Ac20/TsOH/refluxing xylene or TFAA/Et3N/CH2C12/RT or TMSOTf/Et3N/CH2C12/RT results in smooth conversion into the indoline 2 in 50-75% yield depending on the conditions employed.

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Advanced Problems in Organic Reaction Mechanisms by McKillop

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