1,2,3-Dithiazolyl and 1,2,35-Dithiadiazolyl Radicals as Spin-Bearing ...

Compound Name: 3,3′,4,4′-tetraoxo-3,3′,4,4a,4′,8a-hexahydro-1,1′-binaphthyl-6,6′-
diaminium chloride
MW: 417.29 g/mol
Synthesis and Structure:
Appearance:
dark red powder
Lit. and/or notebook #
and page:
DM 11-3, p 3
First made on date:
Jan 10, 2011
Made by:
Dan J. MacDonald
Experimental Data: Pd/C (20 mg) was added to a slurry of 6,6′-dinitro-1,1′-binaphthyl-
3,3′,4,4′-tetraone (1.2291g, 3.0401 mmol) in MeOH (8 mL). A balloon was fitted to the
middle neck of a three neck flask and the system was flushed with H 2 three times. The
balloon was then inflated once more with H 2 and the system was sealed. The reaction
mixture was stirred overnight at room temperature. After 16h the red solution was
filtered to remove the Pd/C and 5 mL of conc. HCl was added and stirred for a 10
minutes. The MeOH was then rotaryevaporated to afford the title compound as a dark red
powder (1.1453g, 2.7448 mmol) 90% yield. Used without further purification.
FTIR (KBr): 3311(m, broad), 1628(s), 1613(s) 1590(s), 1525(s), 1502(s), 1432(w),
1111(w), 1387(w), 1299(s), 1248(s), 1193(s), 1074(m), 1047(m), 1005(s), 912(m),
869(m), 839(m), 825(m), 794(w), 741(m), 716(w), 696(m), 656(w), 581(m), 438(m).
1 HNMR 300 MHz, acetone-d6): δ = 9.17 (d, J = 0.3 Hz, 1H), δ = 7.86 (dd, J = 2.4, J =
7.3 Hz, 1H), δ = 7.47 (s, 1H), δ = 7.40 (d, J = 4.8, 1H), δ = 3.54 (s, broad, 3H).
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