Tetrahedron p. 1667 - 1672 (1984)
Update date:2022-08-04
Topics:
Smith, James G.
Dibble, Peter W.
1,3-Dihydro-1-isobenzofuranol,(1-hydroxyphthalan) and 2-(hydroxymethyl)-benzaldehyde exist in a tautomeric equilibrium.The effects of molecular structure on this equilibrium was examined using various derivatives of dihydroisobenzofuranol.Two effects of this molecular modification were identified: (i) 1-arylmethyl substituents favored the ring-opened tautomer if steric effects arose in the ring closed form and (ii) extending the conjugated system of the dihydroisobensofuran ring (i.e. dihydronaphto<2,3-c> furan also favored the ring opened form.These effects are discussed.
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