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7 CCDC 800884 contains the supplementary
crystallographic data of spiropyran 3i for
this paper. These data can be obtained free of charge from The Cambridge Crystallographic
Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
8
Synthetic Procedure
for Spiropyrans 3
A solution of (1R,2R)-1,2-diphenylethane-1,2-diamine (1h, 42.5mg, 0.2 mmol) and hemiacetal esters 2a (67.7mg, 0.2 mmol) in CH2Cl2 (2
mL) was stirred at reflux for 3 d. The mixture was concentrated,
and the residue was purified
by column chromatography
over silica gel to afford 2H-chromene-piperazin-2-one
spiropyran 3c (85.1 mg) in 85% yield
as a single diastereomer. White solid; mp 136-137 ˚C. [α]D
²4 +101.27
(c 2.0, MeCO2Et). ¹H
NMR (300 MHz, CDCl3): δ = 7.43-7.05
(m, 18 H), 5.95 (s, 2 H), 4.67 (s, 2 H), 2.98 (br s, 1 H), 1.18
(s, 9 H). ¹³C NMR (75 MHz, CDCl3): δ = 167.2,
148.1, 144.1, 138.0, 137.9, 137.8, 137.6, 129.0, 128.6, 128.5, 128.4,
128.4, 128.3, 128.2, 128.1, 127.7, 126.6, 123.3, 120.4, 120.2, 117.0,
86.9, 65.8, 58.6, 34.3, 31.4. FT-IR (KBr): 3350, 3033, 2361, 1693,
1489, 1245, 921, 700 cm-¹. Anal. Calcd
for C34H32N2O2: C, 81.57;
H, 6.44; N, 5.60. Found: C, 81.43; H, 6.67; N, 5.82.
