Photoinduced molecular transformations. Part 156. New photoadditions of 2-hydroxy-1,4-naphthoquinones with naphthols and their derivatiyes
作者:Hiroshi Suginome、Atsushi Konishi、Hideo Sakurai、Hiroki Minakawa、Toshihiro Takeda、Hisanori Senboku、Masao Tokuda、Kazuhiro Kobayashi
DOI:10.1016/0040-4020(94)01026-v
日期:1995.1
Dinaphtho[2,1-b;1′,2′-d]furan-12,13-diones are produced in one-step in up to 45% yield by a (3+2) photoaddition of 2-hydroxy-1,4-naphthoquinones with 2-naphthol, while (±)-(6aα,6bβ,12aβ,12bα)-6a,6b,12a,12b-tetrahydro -12b-hydroxydinaphtho[1,2-a;1′,2′-c]cyclobutenes (14–16%), arising from the stereoselective addition of a (2+2) photoaddition, are products in the photoaddition of 2-hydroxy-1,4-naphthoquinone
Dinaphtho [2,1-b; 1',2'-d]呋喃-12,13-二酮一步一步生产,通过2-羟基-1的(3 + 2)光加成法,收率最高可达45%。 4-萘醌与2-萘酚,而(±)-(6aα,6bβ,12aβ,12bα)-6a,6b,12a,12b-四氢-12b-羟基二萘并[1,2-a; 1',2'-c立体选择加成(2 + 2)光加成反应生成的]环丁烯(14–16%)是2-羟基-1,4-萘醌与2-甲氧基萘和乙酸2-萘酯光加成反应的产物。2-羟基-1,4-萘醌与2-甲氧基萘的光加成也得到2-羟基-3-(2-甲氧基萘-1-基)-1,4-萘醌(23%)作为伴随产物。2-羟基-1,4-萘醌与1-甲氧基萘在丙酮中的溶液相似照射,得到顺式由(3 + 2)光加成反应产生的-6a,13a-二氢-13a-甲氧基二萘并[1,2-b; 2',3'-d]呋喃-7,12-二酮的收率为24%。讨论了形成光加合物的可能机理。