The lewis acid catalyzed reaction of trans-hyponitrite ion with alkyl halides

✍ Scribed by G. David Mendenhall

• Book ID: 104216941
• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 119 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)81434-3

✦ Synopsis

Sodium and other inorganic trans-hyponitrites afford tert-alkyl hyponitritea in good yield from the corresponding alkyl bromide or chloride in the presence of weak Lewis acids. Tertiary alkyl hyponitrites have been widely used to initiate free-radical chains in autooxidation and polymerization reactions, 1 most recently in systems designed to mimic autoxidation processes in viva. Z,3 This class of initiators is often preferred because the decomposition ___ rates show little solvent-dependence and negligible induced decomposition even at high concentrations.lp4 Alkyl hyponitrites are also convenient photochemical sources of radicals.5

Trans-tertiary hyponitrites are usually prepared from a tertiary halide and dry silver trans-hyponitrite.

134 The latter can be precipitated from aqueous solutions of hyponitrite ion,