Preparation of 7-Methyl-7-vinylbicyclo[3.2.0]hept-2-ene Via Cyclobutanone Reduction

References

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• We have taken advantage of the diagnostic methyl at C‐7 (Fig 1) to differentiate between the structural epimers using methods previously outlined by Dreiding for the corresponding ketones.8
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• We intend to report on the kinetics of this thermal rearrangement at a later date
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• 13C‐NMR spectral analysis confirmed the structural assignment by comparison with the chemical shifts of commercial tetrahydroindene: 136.1 (CH=), 135.6 ( C=), 129.5 (CH=), 121.1 (CH=), 42.5 (CH), 40.0 (CH2), 35.5 (CH), 33.7 (CH2), 27.9 (CH2), 24.0 (CH3)
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• Whereas Sartori observed that exo‐7‐vinylbicyclo[3.2.0]‐hept‐2‐ene produced predominantly 5‐vinylbicyclo[2.2.1]hept‐2‐ene,2 Dreiding and Danheiser noted the formation of 3‐methylbicyclo‐[4.2.1]nona‐3,7‐dien‐2‐one from endo‐7‐methyl‐exo‐7‐vinylbicyclo‐[3.2.0]hept‐en‐6‐one.10,11
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• Berk Knighton , W. We thank Professor, for performing the mass spectral measurements
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