In general, intramolecular reactions that form rings are often disfavored entropically because it makes a flexible starting
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In general, intramolecular reactions that form rings are often disfavored entropically because it makes a flexible starting material more rigid. In the case of ring-closing metathesis, however, the entropy penalty for the closure is not especially large for most systems, such as the one below used as part of a synthesis of an anti-tumor compound known as epothilone A. Why might that be?
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TBSO THESE OTBS Grubbs II (30 mol %) CH,CI,, 45 °C, 48h 89% 1:1 E:Z isomers TBSO w OTBS N
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It is because of two factors 1 metathesis reactions proceed via a ringopening step which is much more acidic than a ring closing step and 2 the final product is a macrocycle which will be rigid the strain energy required to form a macrocycle is higher than that of an open chain molecule In addition one must also consider the driving force for the reaction G The G term overall comes from two components the enthalpy change of the metathesis reaction ...View the full answer
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Organic Chemistry
ISBN: 978-1118875766
12th Edition
Authors: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
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