Dibenzo[bc,fg][1,4]oxathiapentalene: an elusive molecule?

Virginia Mazzanti; Eduardo Antonio Della Pia; Martyn Jevric; Tue Heesgaard Jepsen; Anders Kadziola; Ole Hammerich; Mogens Brøndsted Nielsen

doi:10.1080/17415993.2013.789515

Dibenzo[bc,fg][1,4]oxathiapentalene: an elusive molecule?

Virginia Mazzanti, Eduardo Antonio Della Pia, Martyn Jevric, Tue Heesgaard Jepsen, Anders Kadziola, Ole Hammerich, Mogens Brøndsted Nielsen

Department of Chemistry

1 Citation (Scopus)

Abstract

Dibenzo[bc,fg][1,4]dithiapentalene (1) has previously been prepared by an intramolecular nucleophilic aromatic substitution (S_NAr) reaction of 9-fluorodibenzo[b,d]thiophen-1-thiol (X, Y S). Instead, subjecting 9-fluorodibenzo[b,d]benzofuran-1-ol (X, Y O) to similar reaction conditions provided a macrocycle (5), as a result of an intermolecular S_NAr cyclization, rather than dibenzo[bc,fg][1,4]dioxapentalene (3). To shed further light on this reaction type, we here present an attempt to prepare the mixed (O,S) compound dibenzo[bc,fg][1,4]xathiapentalene (7) from 9-fluorodibenzo[b,d] thiophen-1-ol (11, X S, Y O). However, like a previous strategy to make this molecule, the attempt failed. We rationalize the results by a computational study of the reaction energetics and profiles of the S_NAr reactions.

Original language	English
Journal	Journal of Sulfur Chemistry
Volume	34
Issue number	6
Pages (from-to)	588-595
Number of pages	8
ISSN	1741-5993
DOIs	https://doi.org/10.1080/17415993.2013.789515
Publication status	Published - 1 Dec 2013

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@article{11c370d44e3747e2bd9522e310be5ae3,

title = "Dibenzo[bc,fg][1,4]oxathiapentalene: an elusive molecule?",

abstract = "Dibenzo[bc,fg][1,4]dithiapentalene (1) has previously been prepared by an intramolecular nucleophilic aromatic substitution (SNAr) reaction of 9-fluorodibenzo[b,d]thiophen-1-thiol (X, Y S). Instead, subjecting 9-fluorodibenzo[b,d]benzofuran-1-ol (X, Y O) to similar reaction conditions provided a macrocycle (5), as a result of an intermolecular SNAr cyclization, rather than dibenzo[bc,fg][1,4]dioxapentalene (3). To shed further light on this reaction type, we here present an attempt to prepare the mixed (O,S) compound dibenzo[bc,fg][1,4]xathiapentalene (7) from 9-fluorodibenzo[b,d] thiophen-1-ol (11, X S, Y O). However, like a previous strategy to make this molecule, the attempt failed. We rationalize the results by a computational study of the reaction energetics and profiles of the SNAr reactions.",

author = "Virginia Mazzanti and {Della Pia}, {Eduardo Antonio} and Martyn Jevric and Jepsen, {Tue Heesgaard} and Anders Kadziola and Ole Hammerich and Nielsen, {Mogens Br{\o}ndsted}",

note = "Special Issue: In memory of Professor Alessandro Degl'Innocenti",

year = "2013",

month = dec,

day = "1",

doi = "10.1080/17415993.2013.789515",

language = "English",

volume = "34",

pages = "588--595",

journal = "Journal of Sulfur Chemistry",

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publisher = "Taylor & Francis",

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TY - JOUR

T1 - Dibenzo[bc,fg][1,4]oxathiapentalene

T2 - an elusive molecule?

AU - Mazzanti, Virginia

AU - Della Pia, Eduardo Antonio

AU - Jevric, Martyn

AU - Jepsen, Tue Heesgaard

AU - Kadziola, Anders

AU - Hammerich, Ole

AU - Nielsen, Mogens Brøndsted

N1 - Special Issue: In memory of Professor Alessandro Degl'Innocenti

PY - 2013/12/1

Y1 - 2013/12/1

N2 - Dibenzo[bc,fg][1,4]dithiapentalene (1) has previously been prepared by an intramolecular nucleophilic aromatic substitution (SNAr) reaction of 9-fluorodibenzo[b,d]thiophen-1-thiol (X, Y S). Instead, subjecting 9-fluorodibenzo[b,d]benzofuran-1-ol (X, Y O) to similar reaction conditions provided a macrocycle (5), as a result of an intermolecular SNAr cyclization, rather than dibenzo[bc,fg][1,4]dioxapentalene (3). To shed further light on this reaction type, we here present an attempt to prepare the mixed (O,S) compound dibenzo[bc,fg][1,4]xathiapentalene (7) from 9-fluorodibenzo[b,d] thiophen-1-ol (11, X S, Y O). However, like a previous strategy to make this molecule, the attempt failed. We rationalize the results by a computational study of the reaction energetics and profiles of the SNAr reactions.

AB - Dibenzo[bc,fg][1,4]dithiapentalene (1) has previously been prepared by an intramolecular nucleophilic aromatic substitution (SNAr) reaction of 9-fluorodibenzo[b,d]thiophen-1-thiol (X, Y S). Instead, subjecting 9-fluorodibenzo[b,d]benzofuran-1-ol (X, Y O) to similar reaction conditions provided a macrocycle (5), as a result of an intermolecular SNAr cyclization, rather than dibenzo[bc,fg][1,4]dioxapentalene (3). To shed further light on this reaction type, we here present an attempt to prepare the mixed (O,S) compound dibenzo[bc,fg][1,4]xathiapentalene (7) from 9-fluorodibenzo[b,d] thiophen-1-ol (11, X S, Y O). However, like a previous strategy to make this molecule, the attempt failed. We rationalize the results by a computational study of the reaction energetics and profiles of the SNAr reactions.

U2 - 10.1080/17415993.2013.789515

DO - 10.1080/17415993.2013.789515

M3 - Journal article

SN - 1741-5993

VL - 34

SP - 588

EP - 595

JO - Journal of Sulfur Chemistry

JF - Journal of Sulfur Chemistry

IS - 6

ER -

Dibenzo[bc,fg][1,4]oxathiapentalene: an elusive molecule?

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