| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5279433 | Tetrahedron Letters | 2007 | 4 Pages |
Abstract
In the reaction of phthalazinium-2-dicyanomethanide with adamantanethione the rare ring system [1,3]thiazolo[2,3-a]phthalazine was obtained. An X-ray crystal structure of the product shows regioselectivity with the thione carbon bonded to the dicyanomethanide terminus of the 1,3-dipole. UV kinetic measurements and DFT calculations showed that the rate of cycloaddition of adamantanethione was significantly slower than that of DMAD and no super-dipolarophile character was exhibited. This arose from exceptional lowering of the HOMO energy of the 1,3-dipole by the cyano substituents.
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Authors
Richard N. Butler, Anthony G. Coyne, Patrick McArdle, Lisa M. Sibley, Luke A. Burke,