Electron-transfer-induced tautomerization in methylindanones: Electronic control of the tunneling rate for enolization

…, T Bally, T Filipiak, A Marcinek, J Gebicki

Index: Bednarek; Zhu; Bally; Filipiak; Marcinek; Gebicki Journal of the American Chemical Society, 2001 , vol. 123, # 10 p. 2377 - 2387

Full Text: HTML

Citation Number: 10

Abstract

The radical cations generated from 4-methyl-and 4, 7-dimethylindanone, as well as their deuterated isotopomers, isolated in Argon matrices, were found to undergo enolization to the corresponding enol radical cations at rates that differ by orders of magnitude. It is shown by quantum chemical calculations that the effect of the remote methyl group in the 4-position is of purely electronic nature in that it stabilizes the unreactive π-radical relative to the ...

Related Articles:

The design and synthesis of novel IBiox N-heterocyclic carbene ligands derived from substituted amino-indanols

[Levy, Jean-Noel; Latham, Christopher M.; Roisin, Loic; Kandziora, Nadine; Fruscia, Paolo Di; White, Andrew J. P.; Woodward, Simon; Fuchter, Matthew J. Organic and Biomolecular Chemistry, 2012 , vol. 10, # 3 p. 512 - 515]

Perhydroindanone derivatives. II. Stability relationships

[House,H.O.; Rasmusson,G.H. Journal of Organic Chemistry, 1963 , vol. 28, p. 31 - 34]

Perhydroindanone derivatives. II. Stability relationships

[House,H.O.; Rasmusson,G.H. Journal of Organic Chemistry, 1963 , vol. 28, p. 31 - 34]

Synthesis of new chiral auxiliaries for 6π-azaelectrocyclization: 4-and 7-alkyl substituted cis-1-amino-2-indanols

[Kobayashi, Toyoharu; Tanaka, Katsunori; Miwa, Junichi; Katsumura, Shigeo Tetrahedron Asymmetry, 2004 , vol. 15, # 2 p. 185 - 188]

An NMR investigation of the Mills-Nixon effect

[Collins, Michael J.; Gready, Jill E.; Sternhell, Sever; Tansey, Charles W. Australian Journal of Chemistry, 1990 , vol. 43, p. 1547 - 1557]

More Articles...