A transannular reaction during lithium ammonia reduction of an α,β-unsaturated ketone |
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| Authors: | R Balasubramanian S Chandrasekhar K Rajagopalan S Swaminathan |
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| Institution: | Department of Organic Chemistry, University of Madras, A.C. College Buildings, Madras 600025, India |
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| Abstract: | The lithium-ammonia reduction of the α,β-unsaturated bicyclic dione 2-methyl-Δ1,6-bicyclo6,4,0]cyclododecene-5,9-dione 1 has been found to give two isomeric products 2α-methyl-5-oxo-6β-tricyclo6,4,0,01,9] dodecan-9α-ol 2 and 2-β-methyl-5-oxo-6β-tricyclo6,4,0,01,9]dodecan-9α-ol 3 involving a transannular reaction. Chemical and spectral evidence are presented to support the assigned structures. The stereochemistry of 2 arid 3 is also discussed. |
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