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The diphenyliodonium-2-carboxylates: An NMR structure investigation

✍ Scribed by Dario Del Mazza; Manfred G. Reinecke; William B. Smith

Publisher
John Wiley and Sons
Year
1980
Tongue
English
Weight
232 KB
Volume
14
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Diphenyliodonium‐2‐carboxylate, phenyl 4‐methylphenyliodonium‐2‐carboxylate and phenyl 5‐methyl‐phenyliodonium‐2‐carboxylate have been examined by ^1^H and ^13^C NMR spectroscopy. Each compound showed one proton considerably upfield from the others. From the two substituted compounds this was deduced to be H‐6 on the ring containing the carboxylate group. Shift reagents and relaxation measurements were used to make the ^13^C chemical shift assignments. These data are most consistent with a cyclic, neutral structure for these iodonium carboxylates. The iodine is in the center of a trigonal bipyramid with the unsubstituted phenyl and carboxylate group apical, which places the C‐6 proton in the shielding region of the adjacent phenyl group.

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