Abstract
The rates of the hexadehydro-Diels-Alder (HDDA) reaction of substrates containing, minimally, a 1,3,8-triyne subunit are reported. Several series of related substrates, differing in the nature of the three-atom tether that links the 1,3-diyne and diynophile, were examined. Seemingly small changes in substrate structure result in large differences in cyclization rate, spanning more than 8 orders of magnitude. The reactivity trends revealed by these studies should prove useful in guiding substrate design and choice of reaction conditions in future applications.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 4578-4581 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 16 |
| Issue number | 17 |
| DOIs | |
| State | Published - Sep 5 2014 |
Bibliographical note
Publisher Copyright:© 2014 American Chemical Society.