The Evaluation of Secondary Amine Protecting Groups for Nitration

Abstract

Abstract Nitramines (for example RDX, HMX and CL‐20) are frequently made by nitrolyzing tertiary amides. While generally high yielding, sometimes the amides can be difficult to remove while keeping any ring systems intact. This study investigates twelve acyl hexahydro‐ s ‐triazines for their ease of conversion into nitramines using four common nitration conditions. Several new amide protecting group have been examined and one (cyclopropanecarboxamide) has been found to be better than those amides currently employed. The amide groups have been found to be nitrolyzable in the following order: Cyclopropyl>Ethyl>Propyl>Methyl> i ‐Propyl≈ t ‐Butyl≈Methoxymethyl≫Hydrogen>Pentafluorophenyl.