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Isomerization of Ninhydrin–Heterocyclic Ketene Aminal Adducts: Kinetic versus Thermodynamic Control, Solvent Dependency and Mechanism
Author(s) -
Chen Nanyang,
Zou Minming,
Tian Xue,
Zhu Fengjuan,
Jiang Danping,
Cheng Jiagao,
Shao Xusheng,
Li Zhong
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402677
Subject(s) - chemistry , ninhydrin , isomerization , aminal , ketene , solvent , organic chemistry , decomposition , computational chemistry , photochemistry , catalysis , biochemistry , amino acid
Ninhydrin and heterocyclic ketene aminals (HKAs) are versatile building blocks in organic chemistry. Reactions of ninhydrin with HKAs initially produced the kinetic products indeno[1,2‐ b ]pyrrol‐4(1 H )‐one derivatives, which could further isomerize to thermodynamic counterparts indeno[2,1‐ b ]pyrrol‐8(1 H )‐ones. The isomerization showed a strong solvent dependency and occurred through a decomposition–reconstruction pathway. This is the first example of isomerization of ninhydrin‐constructed products. The conversion between kinetic and thermodynamic control may be applicable to similar reactions involving ninhydrin or HKAs.