High Pressure Elicits Unexpected Transformations of Plain Nitroaromatics with 4-(Cyclohex-1-en-1-yl)morpholine

Sonia Diab (1) , Ludovik Noël-Duchesneau (1) , Morgane Sanselme (2) , Yoshinori Kondo (1, 3) , Michaël de Paolis (1) , Isabelle Chataigner (1, 4)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 SMS - Sciences et Méthodes Séparatives
3 Tohoku University [Sendai]
4 LCT - Laboratoire de chimie théorique

Reacting simple nitroarenes with the readily available enamine 4‐(cyclohex‐1‐en‐1‐yl)morpholine leads to unexpected reaction sequences under high pressure. Requiring a very low energy input in the absence of any chemical catalyst, the transformation converts simple starting materials into highly substituted polycyclic structures never described before. An unexpected reaction sequence occurs when simple nitroarenes and the readily available enamine 4‐(cyclohex‐1‐en‐1‐yl)morpholine are placed under high pressure. This one‐pot transformation leads to the generation of highly substituted compounds and presents different advantages such as (1) a rapid increase of molecular complexity through converting simple, cheap, and seldom exploited starting materials into polycyclic structures never described before, (2) the absence of chemical catalysts, (3) a very low energy input.

Domaines: Chimie

Sonia Diab, Ludovik Noël-Duchesneau, Morgane Sanselme, Yoshinori Kondo, Michaël de Paolis, et al.. High Pressure Elicits Unexpected Transformations of Plain Nitroaromatics with 4-(Cyclohex-1-en-1-yl)morpholine. European Journal of Organic Chemistry, 2018, 2018 (18), pp.2048-2052. ⟨10.1002/ejoc.201800316⟩. ⟨hal-02024494⟩