A crystallographic study related to intramolecular hydride shifts in polycyclic hydroxy ketones

Robert V Cernik; Gabrielle Anne Craze; Owen S Mills; Ian Watt; Stephen N Whittleton

A crystallographic study related to intramolecular hydride shifts in polycyclic hydroxy ketones

Robert V Cernik, Gabrielle Anne Craze, Owen S Mills, Ian Watt, Stephen N Whittleton

Research output: Contribution to journal › Article › peer-review

Abstract

The crystal structures of p-nitrobenzoate esters I (n = 1-3) were detd. by x-ray anal. I contain imbedded boat-conformation 4-hydroxycyclohexanones whose C(1)-C(4) distances decrease from 2.67 Å in I (n = 1) to 2.480 Å in I (n = 3). The relationship of the structural variation to the barriers and reaction path for the 1,4-hydride transfer in the corresponding alkoxide anions is discussed. [on SciFinder(R)]

Original language	English
Pages (from-to)	685-90
Number of pages	594
Journal	J. Chem. Soc., Perkin Trans. 2
Issue number	4
Publication status	Published - 1984

Keywords

Hydride shift (1,4-, of oxopentacycloalkyl nitrobenzoates, structure in relation to)
Crystal structure
Molecular structure (of oxopentacycloalkyl nitrobenzoates)
Conformation and Conformers (of oxopentacycloalkyl nitrobenzoates, intramol. hydride transfer in relation to)
crystal structure oxopentacycloalkyl nitrobenzoate
pentacycloalkyl nitrobenzoate oxo structure conformation
conformation oxopentacycloalkyl nitrobenzoate
hydride transfer oxopentacycloalkyl nitrobenzoate structure

Cite this

@article{191a19a4d2744e6ebf7507ccf424fe74,

title = "A crystallographic study related to intramolecular hydride shifts in polycyclic hydroxy ketones",

abstract = "The crystal structures of p-nitrobenzoate esters I (n = 1-3) were detd. by x-ray anal. I contain imbedded boat-conformation 4-hydroxycyclohexanones whose C(1)-C(4) distances decrease from 2.67 {\AA} in I (n = 1) to 2.480 {\AA} in I (n = 3). The relationship of the structural variation to the barriers and reaction path for the 1,4-hydride transfer in the corresponding alkoxide anions is discussed. [on SciFinder(R)]",

keywords = "Hydride shift (1,4-, of oxopentacycloalkyl nitrobenzoates, structure in relation to), Crystal structure, Molecular structure (of oxopentacycloalkyl nitrobenzoates), Conformation and Conformers (of oxopentacycloalkyl nitrobenzoates, intramol. hydride transfer in relation to), crystal structure oxopentacycloalkyl nitrobenzoate, pentacycloalkyl nitrobenzoate oxo structure conformation, conformation oxopentacycloalkyl nitrobenzoate, hydride transfer oxopentacycloalkyl nitrobenzoate structure",

author = "Cernik, {Robert V} and Craze, {Gabrielle Anne} and Mills, {Owen S} and Ian Watt and Whittleton, {Stephen N}",

note = "CAN 101:54238 Physical Organic Chemistry 90994-67-5P; 90994-68-6P; 90994-69-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn., crystal and mol. structure, and conformation of, intramol. hydride transfer in relation to)",

year = "1984",

language = "English",

pages = "685--90",

journal = "J. Chem. Soc., Perkin Trans. 2",

issn = "0300-9580",

publisher = "Chemical Society",

number = "4",

}

TY - JOUR

T1 - A crystallographic study related to intramolecular hydride shifts in polycyclic hydroxy ketones

AU - Cernik, Robert V

AU - Craze, Gabrielle Anne

AU - Mills, Owen S

AU - Watt, Ian

AU - Whittleton, Stephen N

N1 - CAN 101:54238 Physical Organic Chemistry 90994-67-5P; 90994-68-6P; 90994-69-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn., crystal and mol. structure, and conformation of, intramol. hydride transfer in relation to)

PY - 1984

Y1 - 1984

N2 - The crystal structures of p-nitrobenzoate esters I (n = 1-3) were detd. by x-ray anal. I contain imbedded boat-conformation 4-hydroxycyclohexanones whose C(1)-C(4) distances decrease from 2.67 Å in I (n = 1) to 2.480 Å in I (n = 3). The relationship of the structural variation to the barriers and reaction path for the 1,4-hydride transfer in the corresponding alkoxide anions is discussed. [on SciFinder(R)]

AB - The crystal structures of p-nitrobenzoate esters I (n = 1-3) were detd. by x-ray anal. I contain imbedded boat-conformation 4-hydroxycyclohexanones whose C(1)-C(4) distances decrease from 2.67 Å in I (n = 1) to 2.480 Å in I (n = 3). The relationship of the structural variation to the barriers and reaction path for the 1,4-hydride transfer in the corresponding alkoxide anions is discussed. [on SciFinder(R)]

KW - Hydride shift (1,4-, of oxopentacycloalkyl nitrobenzoates, structure in relation to)

KW - Crystal structure

KW - Molecular structure (of oxopentacycloalkyl nitrobenzoates)

KW - Conformation and Conformers (of oxopentacycloalkyl nitrobenzoates, intramol. hydride transfer in relation to)

KW - crystal structure oxopentacycloalkyl nitrobenzoate

KW - pentacycloalkyl nitrobenzoate oxo structure conformation

KW - conformation oxopentacycloalkyl nitrobenzoate

KW - hydride transfer oxopentacycloalkyl nitrobenzoate structure

M3 - Article

SN - 0300-9580

SP - 685

EP - 690

JO - J. Chem. Soc., Perkin Trans. 2

JF - J. Chem. Soc., Perkin Trans. 2

IS - 4

ER -

A crystallographic study related to intramolecular hydride shifts in polycyclic hydroxy ketones

Abstract

Keywords

Fingerprint

Cite this