New Records for Sterically Congested Stilbenes: (E)- and (Z)-1-(2,2-Dimethyl-1-tetralinylidene)-2,2-dimethyltetralin

Dieter Lenoir; James E. Gano; Bong Ser Park; A. Alan Pinkerton

doi:10.1021/jo00296a027

New Records for Sterically Congested Stilbenes: (E)- and (Z)-1-(2,2-Dimethyl-1-tetralinylidene)-2,2-dimethyltetralin

Dieter Lenoir
, James E. Gano
, Bong Ser Park
, A. Alan Pinkerton

Department of Chemistry

University of Bayreuth
University of Toledo

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

14 Scopus citations

Abstract

The synthesis and characterization of the isomeric, highly distorted stilbenes 5b and 6b, are reported. X-ray analysis showed 5b to be twisted 36.7ͦ at the central double bond. Isomer 6b was unstable at room temperature, isomerizing back to 5b with Ea = 21°1.8 kcal/mol. MMP2 calculations, supported by direct observations, suggested 6b was an unsymmetrical structure twisted 73ͦ about the central double bond.

Original language	English
Pages (from-to)	2688-2693
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	55
Issue number	9
DOIs	https://doi.org/10.1021/jo00296a027
State	Published - 1990

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title = "New Records for Sterically Congested Stilbenes: (E)- and (Z)-1-(2,2-Dimethyl-1-tetralinylidene)-2,2-dimethyltetralin",

abstract = "The synthesis and characterization of the isomeric, highly distorted stilbenes 5b and 6b, are reported. X-ray analysis showed 5b to be twisted 36.7ͦ at the central double bond. Isomer 6b was unstable at room temperature, isomerizing back to 5b with Ea = 21°1.8 kcal/mol. MMP2 calculations, supported by direct observations, suggested 6b was an unsymmetrical structure twisted 73ͦ about the central double bond.",

author = "Dieter Lenoir and Gano, \{James E.\} and Park, \{Bong Ser\} and Pinkerton, \{A. Alan\}",

year = "1990",

doi = "10.1021/jo00296a027",

language = "English",

volume = "55",

pages = "2688--2693",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - New Records for Sterically Congested Stilbenes

T2 - (E)- and (Z)-1-(2,2-Dimethyl-1-tetralinylidene)-2,2-dimethyltetralin

AU - Lenoir, Dieter

AU - Gano, James E.

AU - Park, Bong Ser

AU - Pinkerton, A. Alan

PY - 1990

Y1 - 1990

N2 - The synthesis and characterization of the isomeric, highly distorted stilbenes 5b and 6b, are reported. X-ray analysis showed 5b to be twisted 36.7ͦ at the central double bond. Isomer 6b was unstable at room temperature, isomerizing back to 5b with Ea = 21°1.8 kcal/mol. MMP2 calculations, supported by direct observations, suggested 6b was an unsymmetrical structure twisted 73ͦ about the central double bond.

AB - The synthesis and characterization of the isomeric, highly distorted stilbenes 5b and 6b, are reported. X-ray analysis showed 5b to be twisted 36.7ͦ at the central double bond. Isomer 6b was unstable at room temperature, isomerizing back to 5b with Ea = 21°1.8 kcal/mol. MMP2 calculations, supported by direct observations, suggested 6b was an unsymmetrical structure twisted 73ͦ about the central double bond.

UR - https://www.scopus.com/pages/publications/0000461978

U2 - 10.1021/jo00296a027

DO - 10.1021/jo00296a027

M3 - Article

AN - SCOPUS:0000461978

SN - 0022-3263

VL - 55

SP - 2688

EP - 2693

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 9

ER -

New Records for Sterically Congested Stilbenes: (E)- and (Z)-1-(2,2-Dimethyl-1-tetralinylidene)-2,2-dimethyltetralin

Abstract

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