Preparation of 3-(9-Anthryl)acrylates and 9-Aroylethenylanthracenes as Pi-Extended Anthracenes and Their Diels–Alder Type Adducts with Electron-Poor Dienophiles

Hasnaa Sadeq; Thies Thiemann; John P. Graham; Yosef al Jasem; Bernhard Bugenhagen; Nathir Al-Rawashdeh; Mazen al Sulaibi

doi:10.1080/10406638.2016.1220962

Preparation of 3-(9-Anthryl)acrylates and 9-Aroylethenylanthracenes as Pi-Extended Anthracenes and Their Diels–Alder Type Adducts with Electron-Poor Dienophiles

Hasnaa Sadeq, Thies Thiemann, John P. Graham, Yosef al Jasem, Bernhard Bugenhagen, Nathir Al-Rawashdeh, Mazen al Sulaibi

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

2 Citations (Scopus)

Abstract

(E)-3-(9-Anthryl)acrylates and (E)-9-aroylethenylanthracenes have been prepared by solventless Wittig olefination with conjugated phosphoranes. The (E)-3-(9-anthryl)acrylates were brominated to give (E)-3[10-{9-bromoanthryl}]acrylates, which could be subjected to Suzuki reactions with arylboronic acids to produce (E)-3-[10-{9-arylanthryl}]acrylates as pi-extended systems. The compounds thus prepared were subjected to Diels–Alder reactions, partly under solventless conditions.

Original language	English
Pages (from-to)	148-160
Number of pages	13
Journal	Polycyclic Aromatic Compounds
Volume	37
Issue number	2-3
DOIs	https://doi.org/10.1080/10406638.2016.1220962
Publication status	Published - 27 May 2017
Externally published	Yes

Keywords

Anthracenes
Suzuki–Miyaura cross-coupling
pi-extended systems
solventless Diels–Alder reaction
solventless Wittig olefination

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10.1080/10406638.2016.1220962

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Sadeq, H., Thiemann, T., Graham, J. P., al Jasem, Y., Bugenhagen, B., Al-Rawashdeh, N., & al Sulaibi, M. (2017). Preparation of 3-(9-Anthryl)acrylates and 9-Aroylethenylanthracenes as Pi-Extended Anthracenes and Their Diels–Alder Type Adducts with Electron-Poor Dienophiles. Polycyclic Aromatic Compounds, 37(2-3), 148-160. https://doi.org/10.1080/10406638.2016.1220962

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title = "Preparation of 3-(9-Anthryl)acrylates and 9-Aroylethenylanthracenes as Pi-Extended Anthracenes and Their Diels–Alder Type Adducts with Electron-Poor Dienophiles",

abstract = "(E)-3-(9-Anthryl)acrylates and (E)-9-aroylethenylanthracenes have been prepared by solventless Wittig olefination with conjugated phosphoranes. The (E)-3-(9-anthryl)acrylates were brominated to give (E)-3[10-{9-bromoanthryl}]acrylates, which could be subjected to Suzuki reactions with arylboronic acids to produce (E)-3-[10-{9-arylanthryl}]acrylates as pi-extended systems. The compounds thus prepared were subjected to Diels–Alder reactions, partly under solventless conditions.",

keywords = "Anthracenes, Suzuki–Miyaura cross-coupling, pi-extended systems, solventless Diels–Alder reaction, solventless Wittig olefination",

author = "Hasnaa Sadeq and Thies Thiemann and Graham, {John P.} and {al Jasem}, Yosef and Bernhard Bugenhagen and Nathir Al-Rawashdeh and {al Sulaibi}, Mazen",

note = "Publisher Copyright: {\textcopyright} 2017 Taylor & Francis Group, LLC.",

year = "2017",

month = may,

day = "27",

doi = "10.1080/10406638.2016.1220962",

language = "English",

volume = "37",

pages = "148--160",

journal = "Polycyclic Aromatic Compounds",

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Sadeq, H, Thiemann, T, Graham, JP, al Jasem, Y, Bugenhagen, B, Al-Rawashdeh, N & al Sulaibi, M 2017, 'Preparation of 3-(9-Anthryl)acrylates and 9-Aroylethenylanthracenes as Pi-Extended Anthracenes and Their Diels–Alder Type Adducts with Electron-Poor Dienophiles', Polycyclic Aromatic Compounds, vol. 37, no. 2-3, pp. 148-160. https://doi.org/10.1080/10406638.2016.1220962

TY - JOUR

T1 - Preparation of 3-(9-Anthryl)acrylates and 9-Aroylethenylanthracenes as Pi-Extended Anthracenes and Their Diels–Alder Type Adducts with Electron-Poor Dienophiles

AU - Sadeq, Hasnaa

AU - Thiemann, Thies

AU - Graham, John P.

AU - al Jasem, Yosef

AU - Bugenhagen, Bernhard

AU - Al-Rawashdeh, Nathir

AU - al Sulaibi, Mazen

PY - 2017/5/27

Y1 - 2017/5/27

N2 - (E)-3-(9-Anthryl)acrylates and (E)-9-aroylethenylanthracenes have been prepared by solventless Wittig olefination with conjugated phosphoranes. The (E)-3-(9-anthryl)acrylates were brominated to give (E)-3[10-{9-bromoanthryl}]acrylates, which could be subjected to Suzuki reactions with arylboronic acids to produce (E)-3-[10-{9-arylanthryl}]acrylates as pi-extended systems. The compounds thus prepared were subjected to Diels–Alder reactions, partly under solventless conditions.

AB - (E)-3-(9-Anthryl)acrylates and (E)-9-aroylethenylanthracenes have been prepared by solventless Wittig olefination with conjugated phosphoranes. The (E)-3-(9-anthryl)acrylates were brominated to give (E)-3[10-{9-bromoanthryl}]acrylates, which could be subjected to Suzuki reactions with arylboronic acids to produce (E)-3-[10-{9-arylanthryl}]acrylates as pi-extended systems. The compounds thus prepared were subjected to Diels–Alder reactions, partly under solventless conditions.

KW - Anthracenes

KW - Suzuki–Miyaura cross-coupling

KW - pi-extended systems

KW - solventless Diels–Alder reaction

KW - solventless Wittig olefination

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U2 - 10.1080/10406638.2016.1220962

DO - 10.1080/10406638.2016.1220962

M3 - Article

AN - SCOPUS:84984690299

SN - 1040-6638

VL - 37

SP - 148

EP - 160

JO - Polycyclic Aromatic Compounds

JF - Polycyclic Aromatic Compounds

IS - 2-3

ER -

Preparation of 3-(9-Anthryl)acrylates and 9-Aroylethenylanthracenes as Pi-Extended Anthracenes and Their Diels–Alder Type Adducts with Electron-Poor Dienophiles

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