Chemical and nuclear magnetic resonance studies of 3,3‐diphenyltetrahydrofuran derivatives

Philip S Portoghese, D. A. Williams

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Pyrolytic cyclization of a‐ and β‐methadol methiodides afforded cis and trans isomers of 2‐ethyl‐3,3‐diphenyl‐5‐methyltetrahydrofuran, respectively. Catalytic hydrogenation of 2‐ethyli‐dene‐3,3‐diphenyl‐5‐methyltetrahydrofuran yielded the cis and trans isomers in a 2:1 ratio. The nmr spectra of these and structurally related compounds have been analyzed in terms of a half‐chair conformation for 2‐ethyl‐5‐methyl, 2‐ethyl, and 5‐methyl derivatives. An envelope conformation has been suggested for the compounds containing a double bond at C‐2.

Original languageEnglish (US)
Pages (from-to)307-312
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume6
Issue number3
DOIs
StatePublished - Jan 1 1969

Fingerprint

Isomers
Conformations
Methadyl Acetate
Nuclear magnetic resonance
Derivatives
Cyclization
Hydrogenation

Cite this

Chemical and nuclear magnetic resonance studies of 3,3‐diphenyltetrahydrofuran derivatives. / Portoghese, Philip S; Williams, D. A.

In: Journal of Heterocyclic Chemistry, Vol. 6, No. 3, 01.01.1969, p. 307-312.

Research output: Contribution to journalArticle

@article{9076ad6514054f49accb3ca5941d8180,
title = "Chemical and nuclear magnetic resonance studies of 3,3‐diphenyltetrahydrofuran derivatives",
abstract = "Pyrolytic cyclization of a‐ and β‐methadol methiodides afforded cis and trans isomers of 2‐ethyl‐3,3‐diphenyl‐5‐methyltetrahydrofuran, respectively. Catalytic hydrogenation of 2‐ethyli‐dene‐3,3‐diphenyl‐5‐methyltetrahydrofuran yielded the cis and trans isomers in a 2:1 ratio. The nmr spectra of these and structurally related compounds have been analyzed in terms of a half‐chair conformation for 2‐ethyl‐5‐methyl, 2‐ethyl, and 5‐methyl derivatives. An envelope conformation has been suggested for the compounds containing a double bond at C‐2.",
author = "Portoghese, {Philip S} and Williams, {D. A.}",
year = "1969",
month = "1",
day = "1",
doi = "10.1002/jhet.5570060307",
language = "English (US)",
volume = "6",
pages = "307--312",
journal = "Journal of Heterocyclic Chemistry",
issn = "0022-152X",
publisher = "Heterocorporation",
number = "3",

}

TY - JOUR

T1 - Chemical and nuclear magnetic resonance studies of 3,3‐diphenyltetrahydrofuran derivatives

AU - Portoghese, Philip S

AU - Williams, D. A.

PY - 1969/1/1

Y1 - 1969/1/1

N2 - Pyrolytic cyclization of a‐ and β‐methadol methiodides afforded cis and trans isomers of 2‐ethyl‐3,3‐diphenyl‐5‐methyltetrahydrofuran, respectively. Catalytic hydrogenation of 2‐ethyli‐dene‐3,3‐diphenyl‐5‐methyltetrahydrofuran yielded the cis and trans isomers in a 2:1 ratio. The nmr spectra of these and structurally related compounds have been analyzed in terms of a half‐chair conformation for 2‐ethyl‐5‐methyl, 2‐ethyl, and 5‐methyl derivatives. An envelope conformation has been suggested for the compounds containing a double bond at C‐2.

AB - Pyrolytic cyclization of a‐ and β‐methadol methiodides afforded cis and trans isomers of 2‐ethyl‐3,3‐diphenyl‐5‐methyltetrahydrofuran, respectively. Catalytic hydrogenation of 2‐ethyli‐dene‐3,3‐diphenyl‐5‐methyltetrahydrofuran yielded the cis and trans isomers in a 2:1 ratio. The nmr spectra of these and structurally related compounds have been analyzed in terms of a half‐chair conformation for 2‐ethyl‐5‐methyl, 2‐ethyl, and 5‐methyl derivatives. An envelope conformation has been suggested for the compounds containing a double bond at C‐2.

UR - http://www.scopus.com/inward/record.url?scp=84981857651&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84981857651&partnerID=8YFLogxK

U2 - 10.1002/jhet.5570060307

DO - 10.1002/jhet.5570060307

M3 - Article

VL - 6

SP - 307

EP - 312

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

SN - 0022-152X

IS - 3

ER -