Addition of iodine nitrate to olefins

James E. Kropp, Alfred Hassner, Gerald J. Kent

Research output: Contribution to journalArticlepeer-review

5 Scopus citations
Original languageEnglish
Pages (from-to)906-907
Number of pages2
JournalChemical Communications (London)
Issue number15
StatePublished - 1968
Externally publishedYes

Bibliographical note

Funding Information:
Dinitrogen tetr- oxide reacts with iodine to form iodine nitrate, N,O, + I, --+ INO, (8) then addition to the double bond is observed as in reaction (5). The mixture of products observed upon rapid addition of the dinitrogen tetroxide solution can occur through localized formation of iodine nitrate and in competition with the fornia- tion of nitro-iodides. We thank the U.S. Public Health Service, National Center for Air Pollution Control for financial support. (Received, J u n e 4th, 1968, Coin. 720.) If iodine was in the 2j3-position, the C-19 methyl signal should have shifted5 about 0.46 p.p.m. as seen for 2j3-iodo- For formation of nitro-compounds see A. Hassner in L. F. Fieser and M. Fieser, “Reagents for Organic Synthesis”, 3er-nitrocholestane (111). John Wiley, New York, 1967, p. 757; and W. A. Szarek, D. G. Lance, and R. L. Beach, Chem. Comm., 1968, 356. For previous papers see A. Hassner, J. M. Larkin, and J. E. Dowd, J . Org. Chem., 1968,33, 1733. L. Birckenbach and J. Goubeau, Chem. Ber., 1934,67, 1425. G. B. Bachman and T. J. Logan, J . Org. Chem., 1956,21, 1467. T. E. Stevens and W. D. Emmons, J . Amer. Chem. SOC., 1958,80, 338. A. Hassner and F. Boerwinkle, J . Amer. Chem. SOC., 1968,90, 216, and references cited. ti A. Hassner and C. H. Heathcock, J . Org. Chena., 1965, 30, 1748.

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