224967-65-1

Upstream product

• 270901-81-0 N-(1,1-dimethyl-2-[tert-butyldimethylsilanyloxy]propyl)-N-(2-methyl-1-phenylpropyl)-N-oxyl 
• 227000-46-6 1-trimethylsilyloxy-2,2,5-trimethyl-4-phenyl-3-azahexane 3-nitroxide 
• 227000-16-0 N-(2-hydroxy-1,1-dimethylethyl)-α-isopropylnitrone 
• 100-58-3 phenylmagnesium bromide 
• 585-71-7 (1-bromoethyl)benzne 
• 330938-13-1 N-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-N-(2-methyl-1-phenyl-propyl)-O-(1-phenyl-ethyl)-hydroxylamine 
• 227000-80-8 1-trimethylsilyloxy-2,2,5-trimethyl-3-(1-phenylethoxy)-4-phenyl-3-azahexane 
• 227000-39-7 N-(2-trimethylsilyloxy-1,1-dimethylethyl)-α-isopropylnitrone 
• 24292-42-0 (1-phenyl-ethyl)-hydrazine 

Downstream Products

• 330938-08-4 N-[1,1-dimethylethyl-1-(methoxy)]-N-(2-methyl-1-phenylpropyl)-O-(1-phenylethyl)hydroxylamine 

Relevant academic research and scientific papers

Factors influencing the C-O bond homolysis of alkoxyamines: Effects of H-bonding and polar substituents

The synthesis of various new trialkylhydroxylamines is described. The rate constant of the C-O bond cleavage of these new alkoxyamines has been measured. For example, C-O bond homolysis rates in a series of para-substituted TEMPO-styryl compounds TEMPO-CH(CH3)C6H5X 1a (p-MeO), 1b (p-Me), 1d (p-H), 1e (p-Br), and 1f (p-MeO2C) are presented. Furthermore, rate constants for the C-O bond cleavage of α-heteroaryl-substituted secondary alkoxyamines are discussed. A correlation by which the rate constant for the C-O bond cleavage of TEMPO-derived alkoxyamines can be predicted from the C-H BDEs of the corresponding alkanes is presented. Solvent effects as well as the effect of camphorsulfonic acid on the rate of the C-O bond homolysis are discussed. Finally, EPR and kinetic evidence show that alkoxyamines derived from nitroxides which are capable of intramolecular H-bonding undergo C-O bond cleavage faster than the corresponding non-H-bond-forming analogues.

Development of a universal alkoxyamine for "living" free radical polymerizations

Examination of novel alkoxyamines has demonstrated the pivotal role that the nitroxide plays in mediating the "living" or controlled polymerization of a wide range of vinyl monomers. Surveying a variety of different alkoxyamine structures led to α-hydrido derivatives based on a 2,2,5-trimethyl-4-phenyl-3-azahexane-3-oxy, 1, skeleton which were able to control the polymerization of styrene, acrylate, acrylamide, and acrylonitrile based monomers. For each monomer set, the molecular weight could be controlled from 1000 to 200 000 amu with polydispersities typically 1.05-1.15. Block and random copolymers based on combinations of the above monomers could also be prepared with similar control. In comparison with 2,2,6,6-tetramethylpiperidinoxy (TEMPO), these new systems represent a dramatic increase in the range of monomers that can be polymerized under controlled conditions and overcome many of the limitations associated with nitroxide-mediated "living" free radical procedures. Monomer selection and functional group compatibility now approach those of ATRP-based systems.