NOVEL ASPECTS OF THE MANNICH-TYPE REACTION IN BASIC MEDIUM BETWEEN 1,3,6,8-TETRAAZATRICYCLO [4.4.1.1(3,8)] DODECANE (TATD) AND PHENOLS

Rivera, Augusto; Ríos-Motta, Jaime; Quevedo, Rodolfo; Joseph-Nathan, Pedro

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Revista Colombiana de Química

versión impresa ISSN 0120-2804versión On-line ISSN 2357-3791

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RIVERA, Augusto; RIOS-MOTTA, Jaime; QUEVEDO, Rodolfo y JOSEPH-NATHAN, Pedro. NOVEL ASPECTS OF THE MANNICH-TYPE REACTION IN BASIC MEDIUM BETWEEN 1,3,6,8-TETRAAZATRICYCLO [4.4.1.1^3,8] DODECANE (TATD) AND PHENOLS. Rev.Colomb.Quim. [online]. 2005, vol.34, n.2, pp.105-115. ISSN 0120-2804.

Several phenols were tested as nucleophilesin Mannich-type reactions with the macrocyclic aminal 1,3,6,8-tetraazatricyclo[4.4.1.1^3,8]dodecane (TATD) in basic medium. Depending on the degree of substitution of the phenol employed,1,3-bis-[2’-hydroxybenzyl]imidazolidines, 2,6-di[3’-(2’’-hydroxybenzyl)-1’- methyleneimidazolidin] phenols and 3,3’-ethylene-bis-(3,4-dihydro-2H-1,3- benzoxazines) were obtained.

Palabras clave : orto-regioselectivity; Mannich reactions; benzylimidazolidine; bis-benzoxazine.

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