Density Functional Theory Study of Selective Deacylation of Aromatic Acetate in the Presence of Aliphatic Acetate under Ammonium Acetate Mediated Conditions

被引：4

作者：

Xia, Shijing ^{[1
]}

Zhang, Haoyu ^{[2
]}

机构：

[1] Dow Chem Co USA, Engn & Proc Sci R&D, Midland, MI 48674 USA

[2] Dow Chem Co USA, Analyt Technol Ctr, Midland, MI 48674 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 13期

关键词：

P-NITROPHENYL ACETATE; ACYL TRANSFER; DEPROTECTION; HYDROLYSIS; MECHANISMS;

D O I：

10.1021/jo500855g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aromatic acetates can be selectively deprotected in the presence of aliphatic acetates under ammonium acetate mediated condition. B3LYP/6-31++G** level of theory was demonstrated to be successfully used to model the relative reaction rates for deacylation reactions for aliphatic and aromatic ester systems. On the basis of the mechanistic studies, acetate anion is most likely to be the active catalyst for the ester deacylation reactions under ammonium acetate mediated condition.

引用

页码：6135 / 6142

页数：8

共 18 条

[11]

Lowry T. H., 1987, Mechanism and Theory in Organic Chemistry

[12] NaOAc-Mediated Selective Deprotection of Aromatic Acetates and Its Application in the Synthesis of Natural Products [J].

Narender, T. ;

Reddy, K. Papi ;

Madhur, G. .

SYNTHETIC COMMUNICATIONS, 2009, 39 (11) :1949-1956

[13]

Parr RG., 1989, DENSITY FUNCTIONAL T, DOI DOI 10.1007/978-94-009-9027-2_2

[14] A mild, highly selective and remarkably easy procedure for deprotection of aromatic acetates using ammonium acetate as a neutral catalyst in aqueous medium [J].

Ramesh, C ;

Mahender, G ;

Ravindranath, N ;

Das, B .

TETRAHEDRON, 2003, 59 (07) :1049-1054

[15] Harmonic vibrational frequencies: An evaluation of Hartree-Fock, Moller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors [J].

Scott, AP ;

Radom, L .

JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (41) :16502-16513

[16]

Smith M. B., 2007, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure

[17] LOWER LIMIT FOR THE ENERGY DERIVATIVE OF THE SCATTERING PHASE SHIFT [J].

WIGNER, EP .

PHYSICAL REVIEW, 1955, 98 (01) :145-147

[18] Energy barriers for alkaline hydrolysis of carboxylic acid esters in aqueous solution by reaction field calculations [J].

Zhan, CG ;

Landry, DW ;

Ornstein, RL .

JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (32) :7672-7678

← 1 2 →