lecture82012withnotes

lecture82012withnotes - Aziridines and Azetidines Ring...

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Unformatted text preview: Aziridines and Azetidines Ring Strain 3. Pyramidal Inversion and Chirality H 2 N Br n NH Rates of Ring-Closing Reactions Product: Relative Rate: N H 0.07 0.001 HN 100 N H 1 N H 0.002 N H H 2 N Br n NH Rates of Ring-Closing Reactions Product: Relative Rate: embered>6>3>7>4>8 N H 0.07 0.001 5-membered>6>3>7>4>8-10 HN 100 N H 1 N H 0.002 N H H 2 N Br n NH Rates of Ring-Closing Reactions 5-membered>6>3>7>4>8-10 Product: Relative Rate: G = H - T S N H 0.07 0.001 H Enthalpy of activation: RING STRAIN HN 100 N H 1 N H 0.002 N H Rates of Ring-Closing Reactions 5-membered>6>3>7>4>8-10 H 2 N Br n NH G = H - T S Product: Relative Rate: H RING STRAIN embered most stable > 5 >>4>3 N H 0.07 0.001 6-membered, most stable > 5 >>4>3 HN 100 N H 1 N H 0.002 N H Rates of Ring-Closing Reactions 5-membered>6>3>7>4>8-10 H 2 N Br n NH G = H - T S Product: Relative Rate: H RING STRAIN embered most stable > 5 >>4>3 N H 0.07 0.001 6-membered, most stable > 5 >>4>3 HN 100 Medium rings (8-10) transannular interactions N H 1 N H 0.002 N H Rates of Ring-Closing Reactions 5-membered>6>3>7>4>8-10 H 2 N Br n NH G = H - T...
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lecture82012withnotes - Aziridines and Azetidines Ring...

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