Reactivity of Neopentyl-Like Compounds in the Synthesis of Branched Polyethers
Two singly branched symmetrical hexaethers have been synthesized, starting from 2-bromomethyl-2-methyl-1,3-dibromopropane, in a surprisingly efficient one-pot nucleophilic substitution reaction.It is proposed that the expected adverse neopentyl effect is compensated by favourable neighbouring-group participation involving a 'bromonium'-like four-membered-ring transition state.The corresponding trichloride also reacted cleanly, although much more slowly, while the tritosylate gave an oxetane derivative.
Dale, Johannes,Fredriksen, Siw B.
p. 278 - 282
(2007/10/02)
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