Intramolecular [3 + 2] Cycloaddition Reactions of Unsaturated Nitrile Oxides. A Study from the Perspective of Bond Evolution Theory (BET)

2018 ◽  
Vol 122 (37) ◽  
pp. 7472-7481 ◽  
Author(s):  
Abel Idrice Adjieufack ◽  
Vincent Liégeois ◽  
Ibrahim Ndassa Mboumbouo ◽  
Joseph Ketcha Mbadcam ◽  
Benoît Champagne
Keyword(s):  
Cycloaddition Reactions ◽  
Evolution Theory ◽  
Nitrile Oxides ◽  
Unsaturated Nitrile

Spiroheterocycles via Regioselective Cycloaddition Reactions of Nitrile Oxides with 5-Methylene-1H-pyrrol-2(5H)-ones

2010 ◽  
Vol 63 (3) ◽  
pp. 445 ◽  
Author(s):  
Nicola J. Beattie ◽  
Craig L. Francis ◽  
Andris J. Liepa ◽  
G. Paul Savage
Keyword(s):  
Cycloaddition Reaction ◽  
Biphasic System ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Nitrile Oxides ◽  
Facial Selectivity

Substituted 5-methylene-1H-pyrrol-2(5H)-ones underwent a 1,3-dipolar cycloaddition reaction with nitrile oxides to give the corresponding spiro heterocycles. Critical to this reaction was the development of a biphasic system for base-induced dehydrohalogenation of hydroximoyl chlorides, to give nitrile oxides, in the presence of a base-sensitive dipolarophile. A substituted N-tolyl 5-methylene-1H-pyrrol-2(5H)-one exhibited atropisomerism, which in turn led to a 4:1 facial selectivity during cycloaddition.

scholarly journals Cycloaddition reactions of nitrosoalkenes, azoalkenes and nitrile oxides mediated by hydrotalcite

ARKIVOC ◽  
2010 ◽  
Vol 2010 (5) ◽  
pp. 170-182 ◽  
Author(s):  
Americo Lemos ◽  
João Paulo Lourenço
Keyword(s):  
Cycloaddition Reactions ◽  
Nitrile Oxides

Cycloadditions of Alkenylboronic Derivatives

Synthesis ◽  
2020 ◽  
Vol 52 (19) ◽  
pp. 2761-2780
Author(s):  
Oleksandr O. Grygorenko ◽  
Viktoriia S. Moskvina ◽  
Oleksandr V. Hryshchuk ◽  
Andriy V. Tymtsunik
Keyword(s):  
Diels Alder ◽  
Azomethine Ylides ◽  
Cycloaddition Reactions ◽  
Reaction Type ◽  
Nitrile Oxides ◽  
Cyclic Systems

The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addressed less thoroughly in the previous works.1 Introduction2 [2+1] Cycloaddition2.1 Cyclopropanation2.1.1 With Methylene Synthetic Equivalents2.1.2 With Substituted Carbenoids2.2 Epoxidation2.3 Aziridination3 [2+2] Cycloaddition4 [3+2] Cycloaddition4.1 With Nitrile Oxides4.2 With Diazoalkanes4.3 With Nitrones4.4 With Azomethine Ylides5 [4+2] Cycloaddition6 [4+3] Cycloaddition7 Conclusions and Outlook

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