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L. S. BOULOS ET AL.
products 6-[bis(diphenylphosphoryl)methyl]-2,3,4,5-tetrabromo-6-hydroxycyclohexa-2,4-
dien-1-one (25) and methane-1,1-diylbis(diphenylphosphane)dioxide (8). Tetrabromocate-
chol (24) was also isolated and identified by comparing its mp 188–190◦C (Lit. 189–193◦C)
and IR spectra with those of an authentic specimen.
6-[Bis(diphenylphosphoryl)methyl]-2,3,4,5-tetrabromo-6-hydro-
xycyclohexa-2,4-dien-1-one (25)
Eluent: petroleum ether/ethyl acetate (75/25, v/v). Product 25 was separated as green
crystals, yield 0.49 g (61%). mp 223–225◦C. IR (KBr): ν˜ = 1185 (P O), 1435 (P-Ph), 1677
(C O), 3252 (OH) cm−1. 1H NMR (500 MHz, CDCl3): δ = 1.80 (s, 1H, OH, exchangeable
with D2O), 4.02 (dd, JHH = 5.6 Hz, 2JHP = 30 Hz, 1H, Ph2P(O)-CH-P(O)Ph2), 7.37–7.84
(m, 20H, Harom.) ppm. 13C NMR (125 MHz, CDCl3): δ = 30.7 (d, JCP = 130 Hz, C P O),
76.5 (cyclic C-OH, 2JCP = 40.1 Hz), 118.1, 125.3, 128.3, 129.3, 129.6, 131.2, 133.5, 142.9
(aromatic C H), 185.6 (C O) ppm. 31P NMR (CDCl3): δ = 24.3 ppm. MS (EI 70 eV): m/z
(%) = 840 (5) [M+], 638 (25) [M-201]+, 415 (85) [Ph2P(O)CH-P(O)Ph2]+. Anal. Calcd.
for C31H22Br4O4P2 (840.07): C, 44.32; H, 2.64; Br, 38.05; P, 7.37; found: C, 44.30; H,
2.65; Br, 38.15; P, 7.35.
SUPPLEMENTAL MATERIAL
Supplementary data for this article can be accessed on the publisher’s website,
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