Highly facile and stereoselective intramolecular [2 +2]photocycloadditions of bis(alkenoyl)ketenedithioacetals |
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Authors: | Joseph Bubbly K Verghese Babu Sudarsanakumar C Deepa S Viswam Dhanya Chandran Prakash Asokan C V |
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Institution: | School of Chemical Sciences, Mahatma Gandhi University, Kottayam, Kerala, India 686 560. |
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Abstract: | The conformational change induced by the introduction of a ketenedithioacetal moiety at C-4 of 1,7-substituted-1,6-heptadiene-3,5-diones results in favorable spatial relationships between the alkenoyl groups to effect efficient intramolecular cycloadditions: irradiation of bis(alkenoyl)ketenedithioacetals in solution leads to facile and stereospecific intramolecular 2 + 2] photocycloadditions resulting in the formation of substituted bicyclo3.2.0]heptane-2,4-diones, the observed conformational rigidity of which is attributed to the push-pull character of the ketenedithioacetal group. |
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