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Paper | Regular issue | Vol 60, No. 10, 2003, pp.2251-2258
Published online, 25th August, 2003
DOI: 10.3987/COM-03-9848
Photoreaction of 9-Methylbenz[c]acridine with Diphenylacetic Acid in the Chiral Cocrystal

Hideko Koshima,* Ayaka Nakata, Masaki Nagano, and Haitao Yu

*Department of Applied Chemistry, Faculty of Engineering, Ehime University, Matsuyama, 790-8577 Ehime, Japan

Abstract

Despite 9-methylbenz[c]acridine and diphenylacetic acid are achiral molecules, chiral cocrystal was obtained by crystallization from the solution. Irradiation of the enantiomorphous cocrystals caused photodecarboxylation to afford almost racemic photodecarboxylative condensation product as one of the minor products. Reason for the unsuccessful absolute asymmetric photoreaction was discussed based on the molecular arrangement in the lattice.