126583-99-1Relevant articles and documents
CARBOCATIONIC CYCLIZATION. V. REARRANGEMENTS OF 1,2,3-TRIMETHYL-3-(2-R-ALLYL)-4-METHYLENECYCLOBUTENES (R = Me, Ph) IN HSO3F-SO2FCl
Osadchii, S. A.,Shubin, V. G.
, p. 2117 - 2124 (2007/10/02)
It was established by NMR spectroscopy (1H and 13C) that 1,2,3-trimethyl-3-(2-R-allyl)-4-methylenecyclobutenes (R = CH3, C6H5) and 1,5,6,7-tetramethyl-3-R-bicycloheptadienes (R = CH3, C6H5) in the HSO3F-SO2FCl acid system form a mixture of the corresponding stereoisomeric 1,2,6,endo-7- and 1,2,6,exo-7-tetramethyl-4-R-bicyclohept-2,3,4-enyl cations (R = CH3, C6H5).It was shown that neutralization of the acid solutions of the above-mentioned cations of the bicycloheptenyl type, followed by treatment of the neutral products with triphenylmethyl perchlorate, leads to 1,2,3,4-trimethyl-6-R-tropylium perchlorates (R = CH3, C6H5).The possible mechanisms for the formation of the bicycloheptenyl and tropylium cations are discussed.