Macrocyclic diacid 1 was designed and synthesized as an effective catalyst for hemiacetal cleavage. Molecular modelling studies (using Clark Still's MacroModel) show that 1 has many accessible low energy conformations with various degrees of carboxyl group convergence. A straightforward synthesis of 1 was developed (overall yield ca. 19-20%) starting from commercially available 2,6-dihydroxybenzoic acid. In the key-step, a Cs2CO3-mediated reaction under high dilution and slow addition gave the 28-membered ring of 1 as the only non-polymeric product in 45% yield. The dissociation constants of diacid 1 in a 1:1 H2O/MeOH mixture were measured.
A NEW MACROCYCLIC DIACID WITH BALANCED CONFORMATIONAL FLEXIBILITY AND PREORGANIZATION / C.M.A. Gennari, F.E. Molinari, M. Bartoletti, D. Potenza. - In: GAZZETTA CHIMICA ITALIANA. - ISSN 0016-5603. - 122:8(1992), pp. 279-282.
A NEW MACROCYCLIC DIACID WITH BALANCED CONFORMATIONAL FLEXIBILITY AND PREORGANIZATION
C.M.A. GennariPrimo
;F.E. MolinariSecondo
;D. PotenzaUltimo
1992
Abstract
Macrocyclic diacid 1 was designed and synthesized as an effective catalyst for hemiacetal cleavage. Molecular modelling studies (using Clark Still's MacroModel) show that 1 has many accessible low energy conformations with various degrees of carboxyl group convergence. A straightforward synthesis of 1 was developed (overall yield ca. 19-20%) starting from commercially available 2,6-dihydroxybenzoic acid. In the key-step, a Cs2CO3-mediated reaction under high dilution and slow addition gave the 28-membered ring of 1 as the only non-polymeric product in 45% yield. The dissociation constants of diacid 1 in a 1:1 H2O/MeOH mixture were measured.
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