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

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

1 Scopus citations

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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10.1021/jo01304a029

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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",

issn = "0022-3263",

number = "16",

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T1 - Carbon-13 Nuclear Magnetic Resonance Spectra of 5,10-Secosteroids. A Transannular Intramolecular Hydrogen Bond

AU - Highet, Robert J.

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.

UR - https://www.scopus.com/pages/publications/33847085317

U2 - 10.1021/jo01304a029

DO - 10.1021/jo01304a029

M3 - Article

AN - SCOPUS:33847085317

SN - 0022-3263

VL - 45

SP - 3286

EP - 3289

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 16

ER -

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

Abstract

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