@article{01d31962f68b420f85dbc28da066b3c0,
title = "Selective functionalization of unactivated methine positions. 4-Acetyldiamantane",
abstract = "Irradiation of diamantane and biacetyl in methylene chloride gives in 64% yield a mixture of 4-(apical)-acetyl- (2) and 1-(medial)-acetyl-diamantane (3) in 5·5 : 1 ratio (17 : 1 after statistical correction); methylene (3-) attack is not observed.",
author = "Iwao Tabushi and Shosuke Kojo and Schleyer, {Paul V.R.} and Gund, {Tamara M.}",
note = "Funding Information: 138.0-138.5{"} (from MeOH- H,O), and a 1: 1 mixture (0.07 g) of (2) and (3)were obtained. Further purification (column chromatography, sublimation, and recrystallization from MeOH-H20) gave pure (3),m.p. 116-5-117{"}. The combined yield of (2)and (3)based on consumed diamantane was 64%. Although the spectral properties of (2)and (3)were consistent with their structures, definitive proof was obtained by Baeyer- Villiger oxidation' to the known 1-and 4-diamantanols (4) and (5).2 COMe iii 'overall i OH Reagents: i, H,O,, HOAc, H+; ii, OH-, MeOH. The 4-acetyl derivative (2) obtained by this method provides a convenient starting material for further derivat- ization of the apical position of diamantane (1).2-4 The result is also significant because of current interest in the development of methods for the selective attack of methine positions when more than one is present in the same molecule.* This work was supported at Princeton by the National Institutes of Health and by Hoffmann-La Roche, Inc., Nutley, New Jersey. (Received, 20th March 1974; Conz. ",
year = "1974",
doi = "10.1039/C39740000591",
language = "English (US)",
pages = "591",
journal = "Journal of the Chemical Society, Chemical Communications",
issn = "0022-4936",
publisher = "Royal Society of Chemistry",
number = "15",
}