Ring Transformation of 1,5‐Diazabicyclo[3.1.0]hexanes under the Action of Arylketenes.

Abstract

Pyrazole derivatives R 0180Ring Transformation of 1,5-Diazabicyclo[3.1.0]hexanes under the Action of Arylketenes. -The interaction of diazabicyclohexanes (I) and (IV) with arylketenes derived from acylchlorides (II) and (V) yields the monocyclic arylacetyl pyrazolidines (III) and (VI) instead of the expected bicycles. Taking into account that the absence of substituents at position 6 of (IV) decreases the steric disfavor for ring closure the cyclization to the expected bicyclic product, e.g. (VIII) and (X), may occur by a thermodynamically-controlled process. The cyclization can proceed both by a concerted and by a two-step mechanism. -(SHEVTSOV, A. V.; KUZNETSOV, V. V.; KISLUKHIN, A. A.; PETUKHOVA, V. Y.; STRELENKO, Y. A.; MAKHOVA*, N. N.; LYSSENKO, K. A.; J. Heterocycl. Chem. 43 (2006) 4, 881-888; Zelinsky Inst. Org.

Thermal Decomposition Research on 1,5‐Diazabicyclo[3.1.0] Hexane (DABH) as a Potential Low‐toxic Liquid Hypergolic Propellant

“…As Vishnevskiy and Gessner demonstrated [7,17] diaziridine derivatives are potential high-energy materials, which contain two nitrogen atoms in a three-membered ring and can be considered as strained hydrazines. At present, the researches of DABH and its derivatives are limited to organic synthesis as solvent or reagent [8,9], biology pharmaceutical [10], and electrochemistry researches [11]. However, few literatures reported the application of DABH as LHPs.…”