@article{98188e1c444c49c78d0009e5c56a9e1a,
title = "Organometallic compounds in organic synthesis: Nucleophilic substitution reactions of N-methylindoletricarbonyl chromium(0)",
abstract = "The chromium tricarbonyl complex of N-methylindole undergoes nucleophilic substitution reactions with generation of 7-substituted indoles.",
author = "Kozikowski, {Alan P.} and Kimiaki Isobe",
note = "Funding Information: 3 The use of other nitrogen protecting groups (preferably e1et:tron withdrawing) may offer some advantages in extending this process, however. We thank H.R.S.F. (Health Research and Services Foundation) of Pittsburgh, Pennsylvania, and the National Institutes of Health, for support and the Alfred P. Sloan Foundation for a Fellowship during 1978-1980 (to A.P.K.). (Received, 8th August 1978; Corn. 872.) t The preparation of the ring deuteriated dihydroindole is also possible as was shown lty quenching the reaction mixture with deuterium chloride in methanol. 1The following reagents failed to give nucleophilic substitution products : PhC-HCO,-, AYeC-HCO,Et, S[CH,],SC-Me, and cycle-hexyl-N=CHCH,-. -A. P. Kozikowski and M. P. Kuniak, J. Org. Clzem., 1978, 43, 2083. 2 R. J. Card and W. S. Trahanovsky, Tetrahedron Letters, 1973, 3823. 3 M. F. Semmelhack and H. T. Hall, Jr., J. Amev. Chem. Soc., 1974, 96, 7091, 7092; M. F. Seinmelhack, H. T. Hall, Jr., RI. Yoshifuji,and G. Clark, ibid., 1975, 97, 1247; M. G. Semmelhack, H. T. Hall, Jr., and M. Yoshifuji, ibid, 1976, 98, 6387. W. E. Silverthorn, Adv. Ovga?zometallic Chem., 1975, 13, 47. E. 0. Fischer, H. A. Goodwin, C. G. Kreiter, H. D. Simmons, Jr., K. Sonogashira, and S. 5.Wild, J. Ovganometallic Clzem., 1968, 14, 359. H. Plieninger, Chem. Bey., 1954, 87, 127. 7 S. P. Hireniath and R. S. Hosmane, in 'Advances in Heterocyclic Chemistry,' eds. A. R Szatritzky and A. J. Boulton, Academic Press, New York, 1973, vol. 15, p. 277.",
year = "1978",
doi = "10.1039/C39780001076",
language = "English (US)",
pages = "1076--1077",
journal = "Journal of the Chemical Society, Chemical Communications",
issn = "0022-4936",
publisher = "Royal Society of Chemistry",
number = "23",
}