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Preparation of 1-substituted bicyclo[3.2.1]octanes by a rearrangement reaction

โœ Scribed by A.W. Chow; D.R. Jakas; J.R.E. Hoover


Publisher
Elsevier Science
Year
1966
Tongue
French
Weight
188 KB
Volume
7
Category
Article
ISSN
0040-4039

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The 'H and I3C NMR spectra of six bromo-and methoxybicyclo[3.2.1]octanes were completely assigned. An axial bromine substituent at C-2 or C-4 results in a 5 ppm upfield shift of C-8 due to the gauche interaction. An equatorial bromine results in an upfield shift of similar magnitude on either C-6 (o

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The bicyclo[3.2.l]octane ring system is assembled by a three-step process featuring a thermally induced [4+2] cycloaddition followed by a 1,3benzodithiolium ion mediated cyclization onto an enol or silyl enol ether double bond. The bicyclo[3.2.l]octane carbon skeleton is a common structural subunit