Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 1, Pages 280-283Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo7018416
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- NIGMS NIH HHS [S06 GM076168-01] Funding Source: Medline
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[GRAPHICS] Computations provide insight to the stability and isomeric possibilities of thiotropocin, tropodithietic acid, and troposulfenin. Thiotropocin and tropodithietic acid contain a flat 7-membered ring and delocalized pi-bonds similar to those of tropylium ion (C7H7+). Troposulfenin is far less stable; it contains a puckered tropone ring and localized bonds similar to 1,3,5-cycloheptatriene. A facile 1,5-hydrogen shift suggests that thiotropocin and tropodithietic acid exist as a pair of interconverting tautomers. Loss of an acidic proton from these three tautomers produces the same conjugate base structure.
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