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P. J. Heaphy et al. / Tetrahedron Letters 52 (2011) 6359–6362
O
O
O
OH
H
OH
O
+
Cannizaro
2
Esterfication
16
18
19
20
Scheme 5. Final formation of benzyl alcohol (18), benzoic acid (19), and benzyl benzoate (20).
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steps, we have taken pure benzaldehyde in toluene and refluxed
over one week. Indeed, we observed benzyl alcohol, benzoic acid,
and benzyl benzoate, Scheme 5.
In summation, we have synthesized the 1-iodocubane-4-car-
boxaldehyde (6) in a four step process from dimethyl 1,4-cuban-
edicarboxylate (9). We subjected the aldehyde to refluxing
toluene and monitored the formation and disappearance of
compounds. Although the initially hypothesized 4-carboxalde-
hyde-trans-b-iodostyrene (8) was not observed we have proposed
possible mechanistic explanations for the formation of the
benzaldehyde, benzyl alcohol, benzoic acid, and benzyl benzoate.
Acknowledgments
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The authors thank the Niagara University Academic Center for
Integrated Science and the Rochester Academy of Science for their
financial support.
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