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Substituent effects on the ring-chain tautomerism of 1,3-oxazines

✍ Scribed by Ferenc Fülöp; László Lázár; Gábor Bernáth; Reijo Sillanpää; Kalevi Pihlaja

Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
518 KB
Volume
49
Category
Article
ISSN
0040-4020

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✦ Synopsis

Abstmct: The a@ sub&umts at positions 4 and 6 do not erert observable &unmic cffcts on the ting-chain tautomeric mtios of 2,4-or 2,6-aTaqbubstituted-tetmhydm-1,~~.

On the other hand, the ekaivnic @ect of the Z-a~yl subs&em is mat&& in all eight seties s&die4 the equilibria CM be desctibed @ the equation log K-p u + +bg Ko, where u + is the Hammett-Brown conskant of the 2-aryl substituents, end p is a constant charactetistic of the ring system (=0.75*0.05).

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Gas-phase ring-chain tautomeric equilibria with eight 2-phenyl-substituted perhydro-l,3-oxazines and six 2-arylsubstituted 1,2-dihydro-4H-3,l-benzoxazines were studied by recording their mass spectra under different conditions. Their fragmentation behaviour was also studied using metastable ion anal