Nitrile Oxides, Nitrones & Nitronates in Organic Synthesis: by Henry Feuer

By Henry Feuer

A finished systematization of present novel facts in nitrile oxide chemistry, this e-book authoritatively covers systematic concepts at the moment utilized in the coaching and usage of nitrile oxides, nitrones, and nitronates in natural synthesis. It covers elements governing their balance and contains in-depth info on solid and volatile nitrile oxides. With contributions from major specialists, this can be a definitive reference for training pros in natural or medicinal chemistry and a very good textual content for college students learning natural synthesis.

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O O N R 90 (R = H, NO2, 4-, 3-nitrophenyl) 1,3-Dipolar cycloaddition reactions of 2,6-dichlorobenzonitrile oxide with 2 ,3 -didehydro-2 ,3 -dideoxythymidine 91 (R = H, Me3 CMe2 Si), at its 2,5dihydrofuran double bond, gave nucleosides 92 and 93 in 67% yield and 3:2 ratio and 96% yield and 3:1 ratio, respectively (260). O Me NH N O RO 91 O RO O RO O O N 92 R1 R1 N O 93 1,3-Dipolar cycloadditions of benzonitrile oxide, its substituted derivatives as well as 9-anthro- and 2-furonitrile oxides to 5-alkoxy- and 5-hydroxy-2(5H )furanones afforded regiospeciÞcally furoisoxazoles 94.

Cl Cl NOH C NOAlCl3 Cl 30 C Ph Cl 31 Nitrile oxide–BF3 complexes can also be used as electrophilic moieties with aromatic systems. Introducing BF3 into a mixture of 2,6-dichlorobenzonitrile oxide and mesitylene in hexane, gave 88% Z -2 ,6 -dichloro-2,4,6-trimethylbenzophenone oxime (128). Nitrile oxides react in situ with formaldehyde dimethylhydrazone (129) to give oxime-hydrazones RC(:NOH)CH:NNMe2 (R = 4-O2 NC6 H4 , MeCO, MeC (:NOH)). The reaction is performed on treatment of oximes with CH2 :NNMe2 in the presence of Et3 N without isolation of the intermediate nitrile oxides.

4S )-p-Hydroxybenzyl-1,3-oxazolidin-2-one was used as a solid-supported chiral auxiliary in asymmetric 1,3-dipolar cycloadditions (145). It was also shown that Mg(II) cation (from magnesium perchlorate) catalyzes asymmetric 1,3-dipolar cycloaddition reactions using solid-supported oxazolidinone chiral auxiliaries (146). The results obtained support a reaction mechanism, which proposes the coordination of the Mg(II) to the dicarbonyl fragment of the chiral auxiliary. The resin-bound chiral auxiliaries could be recycled once, with little loss in regio- or stereoselectivity, but a second recycle gave products with signiÞcantly decreased regio- and stereoselectivities.

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