Synthetic Applications of Ketene Cycloadditions Lactams and Coumarins

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The objective of this study was to develop new synthetical routes to natural and industrial products utilizing ketene cycioaddition reactions. The cycioaddition of diphenylketene with α,β-unsaturated imines yields (2+2) cycioaddition products, g-lactams. However, electron donating groups, such as dimethylamine, in the 4-position of the α,β-unsaturated imines result in (4+2) cycloaddition products, ∂-lactams. Dichloroketene reacted with α,β-unsaturated imines to yield (4+2) cycloaddition products, g-lactams. Large substituents in the 4-position of a, ^-unsaturated imines resulted in a (2+2) cycioaddition product, β-lactam. The ∂-lactams derived from dichloroketene are easily dehydrochlorinated to the corresponding 2-pyridornes.

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iv, 86 leaves : ill.

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Shieh, Chia Hui August 1984.

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  • Shieh, Chia Hui

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The objective of this study was to develop new synthetical routes to natural and industrial products utilizing ketene cycioaddition reactions. The cycioaddition of diphenylketene with α,β-unsaturated imines yields (2+2) cycioaddition products, g-lactams. However, electron donating groups, such as dimethylamine, in the 4-position of the α,β-unsaturated imines result in (4+2) cycloaddition products, ∂-lactams. Dichloroketene reacted with α,β-unsaturated imines to yield (4+2) cycloaddition products, g-lactams. Large substituents in the 4-position of a, ^-unsaturated imines resulted in a (2+2) cycioaddition product, β-lactam. The ∂-lactams derived from dichloroketene are easily dehydrochlorinated to the corresponding 2-pyridornes.

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iv, 86 leaves : ill.

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  • August 1984

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  • Aug. 22, 2014, 6 p.m.

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  • Jan. 29, 2018, 10:12 a.m.

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Shieh, Chia Hui. Synthetic Applications of Ketene Cycloadditions Lactams and Coumarins, dissertation, August 1984; Denton, Texas. (digital.library.unt.edu/ark:/67531/metadc330680/: accessed June 23, 2018), University of North Texas Libraries, Digital Library, digital.library.unt.edu; .