Structure and metallotropy of mono- and bistrimethylsilyl derivatives of N-acetylacetamide

I. D. Kalikhman; B. A. Gostevskii; O. B. Bannikova; M. F. Larin; O. A. Vyazankina; N. S. Vyazankin

doi:10.1007/BF00954339

Structure and metallotropy of mono- and bistrimethylsilyl derivatives of N-acetylacetamide

I. D. Kalikhman, B. A. Gostevskii, O. B. Bannikova, M. F. Larin, O. A. Vyazankina, N. S. Vyazankin

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Abstract

1. The¹H,²⁹Si NMR and dynamic PMR methods showed that trimethylsilyl derivatives of N-acetyl-acetamide are present in the syn-O-form of Me₃SiOC(CH₃)=NCOCH₃ and this compound is characterized by intramolecular silylotropic 1,5-migration with δG₂₉₈^ne=17.7 ± 0.5 kcal/mole. 2. The bistrimethylsilyl derivative of N-acetylacetamide is a mixture of N,O- and O,O-tautomeric forms that pass into one another as the result of an intramolecular silylotropic N-O-rearrangement with δG₂₉₈^ne=17.7 ± 0.5 kcal/mole. 3. The O,O-form is the characteristic form for dimethylsilyl cyclic derivatives of N-acetylacetamide.

Original language	English
Pages (from-to)	1373-1376
Number of pages	4
Journal	Bulletin of the Academy of Sciences of the USSR Division of Chemical Science
Volume	32
Issue number	7
DOIs	https://doi.org/10.1007/BF00954339
State	Published - 1 Jul 1983
Externally published	Yes

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General Chemistry

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@article{02820c38e02548c8974842dacb9051bd,

title = "Structure and metallotropy of mono- and bistrimethylsilyl derivatives of N-acetylacetamide",

abstract = "1. The1H,29Si NMR and dynamic PMR methods showed that trimethylsilyl derivatives of N-acetyl-acetamide are present in the syn-O-form of Me3SiOC(CH3)=NCOCH3 and this compound is characterized by intramolecular silylotropic 1,5-migration with δG298ne=17.7 ± 0.5 kcal/mole. 2. The bistrimethylsilyl derivative of N-acetylacetamide is a mixture of N,O- and O,O-tautomeric forms that pass into one another as the result of an intramolecular silylotropic N-O-rearrangement with δG298ne=17.7 ± 0.5 kcal/mole. 3. The O,O-form is the characteristic form for dimethylsilyl cyclic derivatives of N-acetylacetamide.",

author = "Kalikhman, {I. D.} and Gostevskii, {B. A.} and Bannikova, {O. B.} and Larin, {M. F.} and Vyazankina, {O. A.} and Vyazankin, {N. S.}",

year = "1983",

month = jul,

day = "1",

doi = "10.1007/BF00954339",

language = "English",

volume = "32",

pages = "1373--1376",

journal = "Bulletin of the Academy of Sciences of the USSR Division of Chemical Science",

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number = "7",

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TY - JOUR

T1 - Structure and metallotropy of mono- and bistrimethylsilyl derivatives of N-acetylacetamide

AU - Kalikhman, I. D.

AU - Gostevskii, B. A.

AU - Bannikova, O. B.

AU - Larin, M. F.

AU - Vyazankina, O. A.

AU - Vyazankin, N. S.

PY - 1983/7/1

Y1 - 1983/7/1

N2 - 1. The1H,29Si NMR and dynamic PMR methods showed that trimethylsilyl derivatives of N-acetyl-acetamide are present in the syn-O-form of Me3SiOC(CH3)=NCOCH3 and this compound is characterized by intramolecular silylotropic 1,5-migration with δG298ne=17.7 ± 0.5 kcal/mole. 2. The bistrimethylsilyl derivative of N-acetylacetamide is a mixture of N,O- and O,O-tautomeric forms that pass into one another as the result of an intramolecular silylotropic N-O-rearrangement with δG298ne=17.7 ± 0.5 kcal/mole. 3. The O,O-form is the characteristic form for dimethylsilyl cyclic derivatives of N-acetylacetamide.

AB - 1. The1H,29Si NMR and dynamic PMR methods showed that trimethylsilyl derivatives of N-acetyl-acetamide are present in the syn-O-form of Me3SiOC(CH3)=NCOCH3 and this compound is characterized by intramolecular silylotropic 1,5-migration with δG298ne=17.7 ± 0.5 kcal/mole. 2. The bistrimethylsilyl derivative of N-acetylacetamide is a mixture of N,O- and O,O-tautomeric forms that pass into one another as the result of an intramolecular silylotropic N-O-rearrangement with δG298ne=17.7 ± 0.5 kcal/mole. 3. The O,O-form is the characteristic form for dimethylsilyl cyclic derivatives of N-acetylacetamide.

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U2 - 10.1007/BF00954339

DO - 10.1007/BF00954339

M3 - Article

AN - SCOPUS:34250143018

SN - 0568-5230

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EP - 1376

JO - Bulletin of the Academy of Sciences of the USSR Division of Chemical Science

JF - Bulletin of the Academy of Sciences of the USSR Division of Chemical Science

IS - 7

ER -

Structure and metallotropy of mono- and bistrimethylsilyl derivatives of N-acetylacetamide

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