Patai's Chemistry of Functional Groups 2009
DOI: 10.1002/9780470682531.pat0035
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Thermal Stereomutations of Cyclopropanes and Vinylcyclopropanes

Abstract: Introduction Historical Synopsis Experimental Studies Correlations of Reaction Rate Constants Theoretical Models and Calculational Results Disparate Kinetic Results Conclusions Acknowledgements

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“…Construction of the more stable trans-divinylcyclopropane, followed by isomerization to cis requires high temperature (approximately 200 °C) and occurs under racemization [19][20][21][22] . Such thermally or photochemically induced homolytic scissions towards diradical intermediates 23 can also trigger the cis-to-trans isomerization of alternatively substituted cyclopropanes and, with appropriate metal complexation for specific substrates, also at lower temperature (80 °C) 24 , albeit under loss of enantiopurity towards the racemic, thermodynamic trans-isomer. Isomerization may also occur in a polar mechanism via zwitterionic intermediates, oxidatively 25 , reductively or under Lewis acid catalysis for specific substrates with the analogous challenges on enantiopurity (that is, its loss) 18 , although remarkable strides towards photochemically assisted chiral resolution with a chiral catalyst have been made recently for specifically substituted cyclopropyl ketones 26,27 .…”
Section: Articlementioning
confidence: 99%
“…Construction of the more stable trans-divinylcyclopropane, followed by isomerization to cis requires high temperature (approximately 200 °C) and occurs under racemization [19][20][21][22] . Such thermally or photochemically induced homolytic scissions towards diradical intermediates 23 can also trigger the cis-to-trans isomerization of alternatively substituted cyclopropanes and, with appropriate metal complexation for specific substrates, also at lower temperature (80 °C) 24 , albeit under loss of enantiopurity towards the racemic, thermodynamic trans-isomer. Isomerization may also occur in a polar mechanism via zwitterionic intermediates, oxidatively 25 , reductively or under Lewis acid catalysis for specific substrates with the analogous challenges on enantiopurity (that is, its loss) 18 , although remarkable strides towards photochemically assisted chiral resolution with a chiral catalyst have been made recently for specifically substituted cyclopropyl ketones 26,27 .…”
Section: Articlementioning
confidence: 99%