Diastereodifferentiating photocyclodimerization of 2-anthracenecarboxylate tethered to cellulose scaffold.
A series of anthracenecarboxylate(AC)-appended 2,3-di-O-methylcelluloses (AC-Cells) of varying degrees of substitution (DS) were synthesized to examine their photochirogenic behavior under a variety of conditions. The product distribution and enantiomeric excess of the cyclodimers obtained upon photoirradiation and the subsequent saponification were critical functions of the DS and conversion, for which a conformational change of the flexible polymer backbone is likely to be responsible.
Fukuhara
Gaku
G
Department of Applied Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan. gaku@chem.eng.osaka-u.ac.jp
Nakamura
Tomohiro
T
Yang
Cheng
C
Mori
Tadashi
T
Inoue
Yoshihisa
Y
D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002482:Cellulose / Q000737:chemistry*; D003500:Cyclization; D019281:Dimerization; D008958:Models, Molecular; D015394:Molecular Structure; D010777:Photochemistry; D013237:Stereoisomerism
C476641:2-anthracenecarboxylate; D000873:Anthracenes; D002264:Carboxylic Acids; D002482:Cellulose