13534-08-2Relevant articles and documents
A General Synthesis of N-Substituted 2-Azaadamantanes and Their 4,8-Disubstituted Derivatives
Henkel, James G.,Faith, William C.,Hane, Jeffrey T.
, p. 3483 - 3486 (1981)
A general synthesis of N-substituted 2-azaadamantanes (1) is reported, along with the corresponding 4,8-dihydroxy derivatives (2).The synthesis offers the advantage of the use of inexpensive and readily available starting material.Dione 3, obtained by decarboxylation of Meerwein's ester, is converted to diene 4 by Bamford-Stevens-type elimination of the corresponding ditosylhydrazone.Epoxidation of 4 affords diepoxide 12, which reacts with primary amines to form the 2-azaadamantyl skeleton 2.Removal of the hydroxyl groups to give 1 is accomplished by using SOCl2 and then LiAlH4.
2,4,4,8,8-Pentanitro-2-Azaadamantane: A High-Density Energetic Compound
Hou, Tianjiao,Ruan, Hongwei,Wang, Guixiang,Luo, Jun
supporting information, p. 6957 - 6960 (2017/12/26)
Polynitroazaadamantanes have a broad application prospect in the field of energetic materials. Herein, the synthesis of 2,4,4,8,8-pentanitro-2-azaadamantane, a new member of the polynitroazaadamantane family, is described in detail. It was prepared through eleven steps in an overall yield of 8.8 %, starting from easily accessible compounds. It shows high thermal stability, an onset decomposition at 254 °C and high density (1.813 g·cm–3).
