Crystal Structure of an Unexpected Oxime-Type Polymer (C10H11BrNO)n

Abstract

Synthesis and crystal structure of oxime-type compounds and their complexes have been a hot topic in recent years 1. Oximes are easily prepared from the corresponding carbonyl compounds with hydroxylamine and its analogues are stable to hydrolysis compared with the corresponding imines. Thus, the electrophilicity of the imino carbon of oximes is lower and addition of nucleophiles to O-substituted oximes does not readily proceed 2. Because the oxime-type compounds are more stable to resist the metathesis of C=N bonds 3 , the introduction of some functional groups or substitutions of some parts with appropriate ones are effective and inevitable. Here, an unexpected oxime-type polymer (C10H11BrNO)n was synthesized and the single crystal structure was also determined. The title compound was synthesized according to an analogous method reported earlier 4. To an ethanolic solution (5 mL) of 3-bromobenzaldehyde (370 mg, 2 mmol) was added an ethanol solution (5 mL) of 1,6-bis(aminooxy)hexane (148.2 mg, 1 mmol). The mixture solution was stirred at 328 K for 4 h. When cooled to room temperature, the precipitate was filtered and washed successively with ethanol and hexane, respectively. The product was dried under vacuum and purified with recrystallization from ethanol to yield 339.9 mg of the title compound, Yield, 65.6 %. Anal. calcd. (%) for (C10H11BrNO)n: