479071-88-0Relevant articles and documents
On rearrangements by cyclialkylations of arylpentanols to 2,3-dihydro-1H-indene derivatives. Part 3. The acid-catalyzed cyclialkylation of 3,4-dimethyl- and 3-([2H3]methyl)-4-methyl-3-phenylpentan-2-ol
Giovannini, Edgardo,Pasquier, Pierre
, p. 1850 - 1855 (2002)
The cyclialkylation of 2-([2H3]methyl)-4-methyl-4-phenyl [1,1,1-2H3]pentan-3-ol (4) yielded a 1:1 mixture of 1,1-di([2H3]methyl)-2,3-dimethyl-1H-indene (5) and of 2,3-dihydro-2,3-di([2H3]methyl)-1,1-dimethyl-1H-indene (6) (Scheme I) [1]. However, it was not clear whether the transposition takes place through the successive migration of a Ph, a Me and again the Ph group (Scheme 2, Path A: shift IV → VII → VIIa) or through Ph-, Me-, and then i-Pr-group (Scheme 2, Path B: IV → VII → VIIb). The cyclialkylation of 3-([2H3]methyl)-4-methyl-3- phenylpentan-2-ol (7) yielded only one product, the 2,3-dihydro-2-([2H3]methyl)-1,1,3-trimethyl-1H-indene (8), in accordance with the migrations according to Path A. This result is also a support for the total mechanism proposed for the cyclialkylation of 4 (Scheme 2). The transition of a tertiary to a secondary carbenium ion is not definitely ensured (see [1]).