Journal Title
Title of Journal: Monatsh Chem
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Abbravation: Monatshefte für Chemie - Chemical Monthly
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Publisher
Springer Vienna
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Authors: Radomir Jasiński
Publish Date: 2015/01/27
Volume: 146, Issue: 4, Pages: 591-599
Abstract
2 + 3 Cycloaddition reactions of nitroacetylene with allenyltype threeatom components take place according to the polar but a onestep mechanism Alternatively to cycloadducts during the reaction between the aforementioned reagents zwitterionic structures with “extended” conformation may be formally created However this route is supported by neither kinetic nor thermodynamic factorsReactions of these TACs with nitroacetylene are a potentially highly effective and selective method of synthesis of nitrosubstituted fivemembered unsaturated heterocycles that are valuable from the point of view of organic preparatory work 10 11 12 For this reason identification of factors determining their course is so important With this in mind the following work was performed 1 an analysis of nature of reagent interactions based on reactivity indices theory and 2 simulations of a theoretically possible reaction path in the presence of a weakly polar toluene and strongly polar medium nitromethane It must be stressed here that the problematics of the 2 + 3 cycloaddition reaction of the aforementioned reagents is also very interesting from a mechanistic point of view These reactions may also take place according to a onestep mechanism as well as to a twostep mechanism with a zwitterionic intermediate 13 14 15 The twostep mechanism is facilitated in this case by 1 the strongly electrophilic character of the dipolarophile and the nucleophilic nature of the TACs and 2 unequal screening of the reaction centres of both reagents
Keywords:
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