Novel Strained Alicyclic Hydrocarbons Based on 5-Methylene-2-norbornene

Abstract

The paper describes the synthesis of novel strained hydrocarbons based on a diene of the norbornene series, namely 5-methylene-2-norbornene, using catalytic cyclopropanation with diazomethane. The study demonstrated the possibility of selective cyclopropanation solely along the endocyclic double bond. The physicochemical properties of the hydrocarbons were investigated systematically. These hydrocarbons were shown to have an advantageous combination of high density, low freezing point, and high energy density value. The study’s findings indicate that the compounds synthesized are promising as a component of high-energy-density fuels for modern jet engines.

High-Energy-Density Liquid Spiro-Norbornanes from Methylenenorbornane

“…Among such hydrocarbons, 5methylene-2-norbornene is one of the most widely available (compound 1, Figure 2). Herein, we prepared the desired compound 1 in a good yield according to the published two-step procedure, 40 including the [4π + 2π] reaction between 3-brompropen-1 and dicyclopentadiene (2), followed by the elimination of hydrogen bromide (Figure 2 and Table S1). Next, based on 1, we obtained two spiro-hydrocarbons (5 and 7, Figure 2) and two other hydrocarbons without spiro-carbon atoms as reference compounds (hydrocarbons 4 and 8, Figure 2).…”