Carbon-13 Nuclear Magnetic Resonance Spectra of 5,10-Secosteroids. A Transannular Intramolecular Hydrogen Bond

Robert J. Highet; Douglas F. Covey; Cecil H. Robinson

doi:10.1021/jo01304a029

Carbon-13 Nuclear Magnetic Resonance Spectra of 5,10-Secosteroids. A Transannular Intramolecular Hydrogen Bond

Robert J. Highet, Douglas F. Covey, Cecil H. Robinson

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Abstract

The 13C NMR resonances of the secosteroids la, 2a, and 3a have been assigned by reference to known models and appropriately deuterated derivatives. A dynamic NMR study of 2a shows an unexpected broadening of the resonances of C-l, -9, and -10 which is attributed to an intramolecular hydrogen bond between the C-10 carbonyl and the C-3 hydroxyl group. This conclusion is supported by studies of solvent effects upon the proton and 13C NMR and infrared spectra.

Original language	English
Pages (from-to)	3286-3289
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	45
Issue number	16
DOIs	https://doi.org/10.1021/jo01304a029
State	Published - Aug 1980

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title = "Carbon-13 Nuclear Magnetic Resonance Spectra of 5,10-Secosteroids. A Transannular Intramolecular Hydrogen Bond",

abstract = "The 13C NMR resonances of the secosteroids la, 2a, and 3a have been assigned by reference to known models and appropriately deuterated derivatives. A dynamic NMR study of 2a shows an unexpected broadening of the resonances of C-l, -9, and -10 which is attributed to an intramolecular hydrogen bond between the C-10 carbonyl and the C-3 hydroxyl group. This conclusion is supported by studies of solvent effects upon the proton and 13C NMR and infrared spectra.",

author = "Highet, {Robert J.} and Covey, {Douglas F.} and Robinson, {Cecil H.}",

year = "1980",

month = aug,

doi = "10.1021/jo01304a029",

language = "English",

volume = "45",

pages = "3286--3289",

journal = "Journal of Organic Chemistry",

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AU - Covey, Douglas F.

AU - Robinson, Cecil H.

PY - 1980/8

Y1 - 1980/8

N2 - The 13C NMR resonances of the secosteroids la, 2a, and 3a have been assigned by reference to known models and appropriately deuterated derivatives. A dynamic NMR study of 2a shows an unexpected broadening of the resonances of C-l, -9, and -10 which is attributed to an intramolecular hydrogen bond between the C-10 carbonyl and the C-3 hydroxyl group. This conclusion is supported by studies of solvent effects upon the proton and 13C NMR and infrared spectra.

AB - The 13C NMR resonances of the secosteroids la, 2a, and 3a have been assigned by reference to known models and appropriately deuterated derivatives. A dynamic NMR study of 2a shows an unexpected broadening of the resonances of C-l, -9, and -10 which is attributed to an intramolecular hydrogen bond between the C-10 carbonyl and the C-3 hydroxyl group. This conclusion is supported by studies of solvent effects upon the proton and 13C NMR and infrared spectra.

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DO - 10.1021/jo01304a029

M3 - Article

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Carbon-13 Nuclear Magnetic Resonance Spectra of 5,10-Secosteroids. A Transannular Intramolecular Hydrogen Bond

Abstract

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