108201-68-9Relevant articles and documents
SPIROCYCLIC MEISENHEIMER COMPLEXES. XIX. STERIC STABILIZATION OF TRINITROCYCLOHEXADIENIDE MEISENHEIMER SPIRO COMPLEXES WITH A 1,3-BENZODIOXOLE RING BY tert-BUTYL GROUPS
Knyazev, V. N.,Liptovtsev, V. N.,Belostotskaya, I. S.,Vol'eva, V. B.,Drozd, V. N.,Ershov, V. V.
, p. 1753 - 1756 (2007/10/02)
The reaction of picryl fluoride with 3,6-di-tert-butylpyrocatechol in the presence of a base leads straight to the formation of a 2',4',6'-trinitrocyclohexadienide Meisenheimer spiro complex with a 4,7-di-tert-butyl-1,3-benzodioxole ring, which is extremely stable even in an acidic medium.The stability is explained by the steric screening of the spirocarbon atom in the complex by the two tert-butyl groups.The analogous complex produced from the sterically less overloaded 3,5-di-tert-butylpyrocatechol is significantly less stable.