Oxidative deamination of aromatic 1,4-imines. A new synthesis of polynuclear aromatic hydrocarbons

Gribble, Gordon W.; Allen, Robert W.; Anderson, Paul S.; Christy, Marcia E.; Colton, C. D.

doi:10.1016/s0040-4039(00)93078-8

Cited by 27 publications

(26 citation statements)

References 13 publications

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“…The intermediate 1,2-naphthalyne (14) may be formed from either 11 or 10, as a strong basic condition always accelerates benzyne [17] formation even by elimination of aromatic protons. Analogous 1,2naphthalyne (14) has also been reported from 1-bromo-2-fluoronaphthalene [18] and 1-bromonaphthalene [19], respectively.…”

Section: Resultssupporting

confidence: 54%

A New Method for the Synthesis of Dinaphtho[1,2‐b;2′,1′‐d]thiophenes and Selenophenes.

et al. 2007

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Organo-selenium compounds S 0130A New Method for the Synthesis of Dinaphtho[1,2-b;2',1'-d]thiophenes and Selenophenes. -The title compounds are best available by treatment of naphthalene-1-sulfonic acid dimethylamides (III) with elemental sulfur or selenium. In this reaction, the C-S/C-Se bonds and the C-C bond are generated in a single step at room temperature. -(ALAM, A.; OHTA, H.; YAMAMOTO, T.; OGAWA*, S.; SATO, R.; Heteroat. Chem. 18 (2007) 3, 239-248; Dep. Chem. Eng., Fac. Eng., Iwate Univ., Morioka, Iwate 020, Japan; Eng.) -H. Toeppel 33-164

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Section: Resultssupporting

confidence: 54%

A New Method for the Synthesis of Dinaphtho[1,2‐b;2′,1′‐d]thiophenes and Selenophenes.

et al. 2007

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“…Gribble and Allen developed a method using aromatic 1,4‐imines to form an aromatic ring via an oxidative deamination reaction. The method consists of the oxidation of a 1,4‐imine into an amine oxide intermediate and subsequent loss of a nitrosoalkane . This transformation could be accomplished by using either H 2 O 2 or m ‐CPBA as oxidant and could be induced by dichlorocarbene generated under phase‐transfer conditions using the Makosza method (Scheme ) .…”

Section: Aromatization Via Extrusion Methodsmentioning

confidence: 99%

“…This transformation could be accomplished by using either H 2 O 2 or m ‐CPBA as oxidant and could be induced by dichlorocarbene generated under phase‐transfer conditions using the Makosza method (Scheme ) . Since 1,4‐imines such as 144 are easily accessible by Diels–Alder reaction of arynes with aza dienes, a multitude of highly substituted CPMs are available including naphthalenes, anthracenes, and benz[ a ]anthracenes, (e.g., 8,9,10,11‐tetrafluorobenz[ a ]anthracene) . It is also worth mentioning that the oxidative deamination of azafulleroids with peracids is an attractive tool to access fullerenes …”

Section: Aromatization Via Extrusion Methodsmentioning

confidence: 99%

Reductive Aromatization/Dearomatization and Elimination Reactions to Access Conjugated Polycyclic Hydrocarbons, Heteroacenes, and Cumulenes

et al. 2017

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Acenes, heteroacenes, conjugated polycyclic hydrocarbons, and polycyclic aromatic hydrocarbons (collectively referred to in this review as conjugated polycyclic molecules, CPMs) have fascinated chemists since they were first isolated and synthesized in the mid 19th century. Most recently, these compounds have shown significant promise as the active components in organic devices (e.g., solar cells, thin‐film transistors, light‐emitting diodes, etc.), and, since 2001, a plethora of publications detail synthetic strategies to produce CPMs. In this review, we discuss reductive aromatization, reductive dearomatization, and elimination/extrusion reactions used to form CPMs. After a brief discussion on early methods to synthesize CPMs, we detail the use of reagents used for the reductive (de)aromatization of precursors containing 1,4‐diols/diethers, including SnCl2 and iodide (I−). Extension of these methods to carbomers and cumulenes is briefly discussed. We then describe low‐valent metal species used to reduce endoxides to CPMs, and discuss the methods to directly reduce acenediones and acenones to the respective acene. In the final section, we describe methods used to affect aromatization to the desired CPM via extrusion of small, volatile molecules.

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“…The intermediate 1,2-naphthalyne (14) may be formed from either 11 or 10, as a strong basic condition always accelerates benzyne [17] formation even by elimination of aromatic protons. Analogous 1,2-naphthalyne (14) has also been reported from 1-bromo-2-fluoronaphthalene [18] and 1-bromonaphthalene [19], respectively.…”

Section: Resultsmentioning

confidence: 55%

A new method for the synthesis of dinaphtho[1,2‐b;2′,1′‐d]thiophenes and selenophenes

Alam

Ohta

Yamamoto

et al. 2007

Heteroatom Chemistry

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Naphthalene-1-sulfonic acid dimethylamides were treated with n-BuLi and elemental sulfur or selenium to afford dinaphtho [1,2-b:2 ,1 -d]thiophenes and selenophenes, respectively. This is the first example of making two C S/Se bonds and a C C bond in a single step at room temperature and also demonstrates a useful method for the synthesis of both thiophenes and selenophenes on naphthalene. In the case of the reactions of elemental selenium, diselenides were also obtained along with

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Oxidative deamination of aromatic 1,4-imines. A new synthesis of polynuclear aromatic hydrocarbons

Cited by 27 publications

References 13 publications

A New Method for the Synthesis of Dinaphtho[1,2‐b;2′,1′‐d]thiophenes and Selenophenes.

A New Method for the Synthesis of Dinaphtho[1,2‐b;2′,1′‐d]thiophenes and Selenophenes.

Reductive Aromatization/Dearomatization and Elimination Reactions to Access Conjugated Polycyclic Hydrocarbons, Heteroacenes, and Cumulenes

A new method for the synthesis of dinaphtho[1,2‐b;2′,1′‐d]thiophenes and selenophenes

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