A study of the oxyanion effect in reactions of 2-methyl-2-propen-1-ol |
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| Affiliation: | 1. Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India;2. Department of Chemistry, Sri Venkateswara University, Tirupati 517502, India;3. Department of Chemistry, S. V. Arts UG & PG College (TTD''S), Tirupati 517502, India;1. Homogeneous Catalysis Laboratory, Department of Chemistry, The University of Burdwan, Golapbag, Burdwan, 713104 WB, India;2. Department of Microbiology, The University of Burdwan, Golapbag, Burdwan, 713104 WB, India;3. K. G. Engineering Institute, Bishnupur, Bankura, WB, India |
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| Abstract: | Optimum conditions for the self reaction of the potassium alkoxide of 2-methyl-2-propen-1-ol to give 3,5,5,-trimethyltetrahydropyran-2-ol (7) have been developed. Evidence is presented to demonstrate that the key carbon carbon bond forming step in this reaction formally involves an unusual type of Ene reaction between 2-methylpropenal and the allylic alkoxide anion in which stepwise or highly asynchronous hydride transfer precedes carbon carbon bond formation. Under different reactions conditions the condensation of 2-methylpropenal with the potassium alkoxide of 2-methyl-2-propen-1-ol proceeds to give the bicyclic lactone, 6-endo-hydroxy-7-exo-(2-methyl allyioxymethyl)-3-oxa-1,5,7-trimethyl bicyclo[3,3,1]nonan-2-one (11), the crystal structure of which is reported. |
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