cas 3172-00-7, 5-BROMO-2-HYDROXYCYCLOHEPTA-2,4,6-TRIEN-1-ONE

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Regioselective nucleophilic substitution of 5-bromo-2-methoxytropone
The reaction of 5-bromo-2-methoxytropone with O- and N-nucleophiles, such as ethanol/potassium carbonate, sodium hydroxide, diethylamine, propylamine, p-chloroaniline/triethylamine, and p-phenylenediamine/triethylamine, gave corresponding 2-O- and 2-N-substituted troponoids. Alkyl diamines reacted with the substrate to produce bis(2-aminotropone)s. In the case of S-nucleophiles as 1-propanethiol, thiophenol, and 4-aminothiophenol with a base, the regioselective substitution at the 5-position occurred. Halogenation reagents, triphenyldibromophosphorane and its dichloro analogue, furnished 2,5-dibromo- and 2,5-dichlorotropones, respectively.
Sato, Ohki,Nitta, Ai,Yamamoto, Ami
p. 644 - 650
(2015/02/05)

A THERMALLY-INDUCED RADICAL REARRANGEMENT OF 2-ARYLMETHOXYTROPONES TO 3- AND 5-ARYLMETHYLTROPOLONES
2-Arylmethoxytropones, i.e., 2-benzyloxytropone, 2-(p-tolylmethoxy)tropone, 2-(4-bromophenylmethoxy)tropone, 2-(4-chlorophenylmethoxy)tropone, 2-(4-methoxyphenylmethoxy)tropone, and 2-(1-naphthylmethoxy)tropone, rearranged upon heating to the 3- and 5-arylmethyltropolones via the radical intermediates.Similarly, 5-bromo-2-(p-tolylmethoxy)tropone gave 5-bromo-3-(p-tolylmethyl)tropolone.
Takeshita, Hitoshi,Mametsuka, Hiroaki,Chisaka, Atsuko,Matsuo, Norihide
p. 73 - 76
(2007/10/02)