79635-09-9Relevant academic research and scientific papers
All Non-Carbon B3NO2 Exotic Heterocycles: Synthesis, Dynamics, and Catalysis
Opie, Christopher R.,Noda, Hidetoshi,Shibasaki, Masakatsu,Kumagai, Naoya
supporting information, p. 4648 - 4653 (2019/03/17)
The B3NO2 six-membered heterocycle (1,3-dioxa-5-aza-2,4,6-triborinane=DATB), comprising three different non-carbon period 2 elements, has been recently demonstrated to be a powerful catalyst for dehydrative condensation of carboxylic acids and amines. The tedious synthesis of DATB, however, has significantly diminished its utility as a catalyst, and thus the inherent chemical properties of the ring system have remained virtually unexplored. Here, a general and facile synthetic strategy that harnesses a pyrimidine-containing scaffold for the reliable installation of boron atoms is disclosed, giving rise to a series of Pym-DATBs from inexpensive materials in a modular fashion. The identification of a soluble Pym-DATB derivative allowed for the investigation of the dynamic nature of the B3NO2 ring system, revealing differential ring-closing and -opening behaviors depending on the medium. Readily accessible Pym-DATBs proved their utility as efficient catalysts for dehydrative amidation with broad substrate scope and functional-group tolerance, offering a general and practical catalytic alternative to reagent-driven amidation.
Organic Peroxides, XIV. The Thermal Decomposition of Polycyclic tert-Butyl Bridgehead Peroxycarboxylates
Ruechardt, Christoph,Golzke, Volker,Range, Guenter
, p. 2769 - 2785 (2007/10/02)
Eleven bridgehead peresters (1, 2, 5 - 8, 10, 12, 14, 18, 21) have been prepared for the first time and the products and the kinetics of their thermal decomposition were investigated.The correlations of all known thermolysis constants of bridgehead peresters with the steric substituent constants φf, with the solvolysis constants of the corresponding bridgehead bromides, as well as with the change in strain enthalpy ΔHsp for hydride abstraction from the bridgehead, as calculated by the procedure of v.R.Schleyer, were analysed.The thermolysis constants of these peresters are mainly determined by the polar effect in the transition state of the perester fragmentation.
