Relative rates of cycloaromatization of dynemicin azabicyclo[7.3.1]enediyne core structures. An unusual change in ΔS‡
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 13,p. 1541-1542
- https://doi.org/10.1039/c39940001541
Abstract
A series of dynemicin core azabicyclo[7.3.1]enediynes undergo cycloaromatization at dramatically different rates despite the fact that the distance (r, by X-ray diffraction) between the bonding acetylenes is practically identical (3.4 Å); when the carbamate protecting group is removed to give the sec-amine 10, it cycloaromatizes more rapidly, and the entropy of activation changes from a negative to positive.Keywords
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