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Mandatory Fields
Butler, RN,Coyne, AG,McArdle, P,Sibley, LM,Burke, LA
2007
September
Tetrahedron Letters
Uncharacteristic thione behavior in a Huisgen cycloaddition reaction: a kinetic and theoretical study
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()
Optional Fields
THIOBENZOPHENONE S-METHYLIDE AZOMETHINE YLIDES 1,3-DIPOLAR CYCLOADDITIONS MULTIPLE BONDS THIOKETONES DIPOLAROPHILES ADAMANTANETHIONE RATES REGIOCHEMISTRY PHTHALAZINIUM
48
6684
6687
In the reaction of phthalazinium-2-dicyanomethanide with adamantanethione the rare ring system [1,3]thiazolo[2,3a]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. (c) 2007 Elsevier Ltd. All rights reserved.
DOI 10.1016/j.tetlet.2007.07.138
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