摘要
为制备多环芳烃中间体,用AlCl3作催化剂,研究了常温常压下,蒽与草酰氯的C-酰基化反应.GC-MS分析了产物组成,GC考察了各因素对蒽转化率和产物选择性的影响.结果表明:反应生成了氯蒽、9-蒽甲酸、9-氯甲酰基-10-蒽甲酸、9-酮酸-9,10-二氢-10-蒽甲醇、9-氯乙基-10-氯乙烯基蒽和9,10-二氢-9,9′-二蒽甲酮等Friedel-Crafts碳正离子无法解释的产物;用碳正离子亲电取代-芳环上自由基亲电取代双反应历程可合理解释"反常产物"的生成;双反应历程可合理解释各因素对蒽转化率和产物选择性的影响.蒽与草酰氯的C-酰基化反应可以制备新型多环芳烃中间体9-氯甲酰基-10-蒽甲酸、1,2-蒽乙二酮和9,10-二氢-9,9′-二蒽甲酮.
To prepare the polycyclic aromatic intermediates, the C-acylation reaction of anthracene with oxalyl chloride over AlCl3 catalyst was investigated under mild conditions, including room temperature and ambient atmosphere. The GC-MS was used to analysis the reaction products. The conversion of anthracene and selectivity of products were calculated according to GC analyses. The results show that chloroanthracene, 9 anthroic acid, 9-carbonyl chloride-10- anthroic acid, 9-carbonyl acid-9,10-dihydro-10-anthracenemethanol, 9-chloroethyl-10-chlorovi- nylanthracene and 9,10-dihydro-9,9r-dianthroicmethanone were obtained, which can not be ex- plained by the Friedel-Crafts pathway of carbonium, but can be reasonably explained by the re- action pathway of electrophilic substitution of carbonium and free radical. The effects of various factors on conversion of anthracene and selectivity of products can also be illuminated by the double reaction pathway. The polycyclic aromatic intermediates of 9-carbonyl chloride-10- anthroic acid, 1,2-aceanthrylenedione and 9,10-dihydro-9,9 Cdianthroicmethanone can be synthesized under optimized conditions.
出处
《中国矿业大学学报》
EI
CAS
CSCD
北大核心
2008年第6期834-838,共5页
Journal of China University of Mining & Technology
基金
国家自然科学基金项目(20207003)
江苏省“青蓝工程”优秀青年骨干教师资助项目(苏教200512)
