Stereochemical π-Facial Selectivity of the Diels-Alder Reaction of Benz[a]aceanthrylene and 1,4-Diphenylbenz[a]aceanthrylene

Benjamin F. Plummer; Saadia Faiz; Ted Wiederhold; Marilyn Wooten; Joseph K. Agyin; Kurt L. Krause; Mitchell D. Miller; William H. Watson

doi:10.1021/jo971610t

Stereochemical π-Facial Selectivity of the Diels-Alder Reaction of Benz[a]aceanthrylene and 1,4-Diphenylbenz[a]aceanthrylene

Benjamin F. Plummer, Saadia Faiz, Ted Wiederhold, Marilyn Wooten, Joseph K. Agyin, Kurt L. Krause, Mitchell D. Miller, William H. Watson

Department of Biochemistry & Structural Biology

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

Abstract

The Diels-Alder (D-A) reaction of the twisted hydrocarbon 1,4-diphenylbenz[a]aceanthrylene (4) with dienophiles maleic anhydride, bromomaleic anhydride, and N-phenylmaleimide and with benzyne is reported. The stereochemistry of the products derived from the D-A reaction of 4 is compared with the products derived from reaction of planar benz[a]aceanthrylene (5) with maleic anhydride as a model. The endo regiochemical π-facial selectivity of 4 appears to be the result of the steric effect of a phenyl substituent as the transition state is reached. Compound 5 produces both endo and exo D-A adducts when treated with maleic anhydride. X-ray crystallographic analysis verifies the topology of the bromomaleic anhydride adduct of 4 and the maleic anhydride adduct of 5.

Original language	English (US)
Pages (from-to)	9290-9294
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	62
Issue number	26
DOIs	https://doi.org/10.1021/jo971610t
State	Published - Jan 1 1997

ASJC Scopus subject areas

Organic Chemistry

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title = "Stereochemical π-Facial Selectivity of the Diels-Alder Reaction of Benz[a]aceanthrylene and 1,4-Diphenylbenz[a]aceanthrylene",

abstract = "The Diels-Alder (D-A) reaction of the twisted hydrocarbon 1,4-diphenylbenz[a]aceanthrylene (4) with dienophiles maleic anhydride, bromomaleic anhydride, and N-phenylmaleimide and with benzyne is reported. The stereochemistry of the products derived from the D-A reaction of 4 is compared with the products derived from reaction of planar benz[a]aceanthrylene (5) with maleic anhydride as a model. The endo regiochemical π-facial selectivity of 4 appears to be the result of the steric effect of a phenyl substituent as the transition state is reached. Compound 5 produces both endo and exo D-A adducts when treated with maleic anhydride. X-ray crystallographic analysis verifies the topology of the bromomaleic anhydride adduct of 4 and the maleic anhydride adduct of 5.",

author = "Plummer, {Benjamin F.} and Saadia Faiz and Ted Wiederhold and Marilyn Wooten and Agyin, {Joseph K.} and Krause, {Kurt L.} and Miller, {Mitchell D.} and Watson, {William H.}",

year = "1997",

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doi = "10.1021/jo971610t",

language = "English (US)",

volume = "62",

pages = "9290--9294",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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T1 - Stereochemical π-Facial Selectivity of the Diels-Alder Reaction of Benz[a]aceanthrylene and 1,4-Diphenylbenz[a]aceanthrylene

AU - Plummer, Benjamin F.

AU - Faiz, Saadia

AU - Wiederhold, Ted

AU - Wooten, Marilyn

AU - Agyin, Joseph K.

AU - Krause, Kurt L.

AU - Miller, Mitchell D.

AU - Watson, William H.

PY - 1997/1/1

Y1 - 1997/1/1

N2 - The Diels-Alder (D-A) reaction of the twisted hydrocarbon 1,4-diphenylbenz[a]aceanthrylene (4) with dienophiles maleic anhydride, bromomaleic anhydride, and N-phenylmaleimide and with benzyne is reported. The stereochemistry of the products derived from the D-A reaction of 4 is compared with the products derived from reaction of planar benz[a]aceanthrylene (5) with maleic anhydride as a model. The endo regiochemical π-facial selectivity of 4 appears to be the result of the steric effect of a phenyl substituent as the transition state is reached. Compound 5 produces both endo and exo D-A adducts when treated with maleic anhydride. X-ray crystallographic analysis verifies the topology of the bromomaleic anhydride adduct of 4 and the maleic anhydride adduct of 5.

AB - The Diels-Alder (D-A) reaction of the twisted hydrocarbon 1,4-diphenylbenz[a]aceanthrylene (4) with dienophiles maleic anhydride, bromomaleic anhydride, and N-phenylmaleimide and with benzyne is reported. The stereochemistry of the products derived from the D-A reaction of 4 is compared with the products derived from reaction of planar benz[a]aceanthrylene (5) with maleic anhydride as a model. The endo regiochemical π-facial selectivity of 4 appears to be the result of the steric effect of a phenyl substituent as the transition state is reached. Compound 5 produces both endo and exo D-A adducts when treated with maleic anhydride. X-ray crystallographic analysis verifies the topology of the bromomaleic anhydride adduct of 4 and the maleic anhydride adduct of 5.

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DO - 10.1021/jo971610t

M3 - Article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 26

ER -

Stereochemical π-Facial Selectivity of the Diels-Alder Reaction of Benz[a]aceanthrylene and 1,4-Diphenylbenz[a]aceanthrylene

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