Photochemical Synthesis of Novel Heterocyclic Compounds Using Flow Micro Reactor

2016 Fiscal Year Final Research Report

• Project/Area Number: 26410049
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Nara Institute of Science and Technology
• Principal Investigator: Mizuno Kazuhiko 奈良先端科学技術大学院大学, 物質創成科学研究科, 客員教授 (10109879)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: フロー系マイクロリアクター / エキシプレックス / 分子内光環化反応 / ヘテロ環化合物 / 光誘起電子移動反応 / [2+2]光環化付加反応 / FEPチューブ

Outline of Final Research Achievements

Intramolecular photocyclization by use of flow micro reactor was examined for synthesis of novel heterocyclic compounds in highly efficient and selective photoreaction. Irradiation of benzene solution containing 1-cyanonaphthalene derivatives tethered by prenyl or vinyloxy group at 2- or 4-position afforded intramolecular [2+2] photocycloadduct as heterocyclic compound. The photoreaction using flow micro reactor (1 mm diameter, 2-5 m length FEP tubing) was much faster than that in the batch system (10 mm diameter, 20 cm length, Pyrex glass tubing). Similar photoreaction of phenanthrene and aniline tethered by methylene chain (n=2~5) afforded spiro-compounds (n=3, 5) and 9-methylene-9,10-dihydrophenanthrene (n=2) in high yields when flow micro reactor system was used.

Free Research Field

光化学