Peri-bridged naphthalenes from 1,8-dilithionaphthalene

Meinwald, Jerrold; Dauplaise, David; Wudl, Fred; Hauser, J. J.

doi:10.1021/ja00443a051

Cited by 94 publications

(42 citation statements)

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“…Naphtho [1,8-c,d]-1,2-diselenole (Se 2 naph) is synthesized using a one-pot reaction starting from naphthalene (26% yield). This synthesis was modelled after one reported by Ashe et al for the sulfur analog naphtho [1,8-c,d] [1,2]dithiole. 6 It was also found that substitution of the naphthalene ring in Se 2 naph with either one tert-butyl group to form 2-tert-butylnaphtho [1,8-c,d] [1,2]diselenole (mt-Se 2 naph) or two tert-butyl groups to form 2,7-di-tert-butylnaphtho [1,8-c,d] [1,2]diselenole (dt-Se 2 naph) was possible via a standard Friedel Crafts alkylation.…”

Section: Resultsmentioning

confidence: 99%

“…This synthesis was modelled after one reported by Ashe et al for the sulfur analog naphtho [1,8-c,d] [1,2]dithiole. 6 It was also found that substitution of the naphthalene ring in Se 2 naph with either one tert-butyl group to form 2-tert-butylnaphtho [1,8-c,d] [1,2]diselenole (mt-Se 2 naph) or two tert-butyl groups to form 2,7-di-tert-butylnaphtho [1,8-c,d] [1,2]diselenole (dt-Se 2 naph) was possible via a standard Friedel Crafts alkylation. 7,15 The addition of dibromine to mt-Se 2 naph gave no reaction between selenium and bromine.…”

Section: Resultsmentioning

confidence: 99%

“…1 In their work, Se 2 naph was synthesized by adding two equivalents of selenium powder to dilithionaphthalene and then exposing the reaction mixture to air to obtain the desired product in 18-22% yield. Today this preparation is still the most referenced procedure for making this In 1994, a synthetic procedure for the sulfur analog, naphtho [1,8-c,d]-1,2-dithiole (S 2 naph) was published using unsubstituted naphthalene as a starting material.…”

Section: Introductionmentioning

confidence: 99%

“…6 We have extended that synthesis to the selenium system and developed a facile, "one-pot" synthesis for Se 2 naph. We have investigated substitution of this ring using Friedel Crafts alkylation and report the synthesis of 2,7-di-tertbutylnaphtho [1,8-c,d] [1,2]diselenole (dt-Se 2 naph) and 2-tert-butylnaphtho [1,8-c,d] [1,2]diselenole (mtSe 2 naph). Reaction of mt-Se 2 naph with bromine gives 4,7-dibromo-2-tert-butylnaphtho [1,8-c,d] [1,2]diselenole (Br 2 -mt-Se 2 naph) ( Figure 2).…”

Section: Introductionmentioning

confidence: 99%

“…Figure 2. 2,7-di-tert-butylnaphtho [1,8-c,d] [1,2]diselenole (dt-Se 2 naph), 2-tert-butylnaphtho [1,8-c,d] [1,2]diselenole (mt-Se 2 naph), and 4,7-dibromo-2-tert-butylnaphtho [1,8-c,d] [1,2]diselenole (Br 2 -mt-Se 2 naph). These compounds can be used as ligands, by reducing the Se-Se bond needs to forming dianionic 10,11,14 These complexes are very similar around the Pt(II) metal center despite the flexibility of the backbone.…”

Section: Introductionmentioning

confidence: 99%

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Platinum Complexes of Aromatic Selenolates

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Several synthetic methods are used to prepare naphthalene based aromatic 1,2-diselenoles. A new one-pot synthesis starting from naphthalene is used to produce the known compound naphtho [1,8-c,d]-1,2-diselenole (Se 2 naph). Friedel Crafts alkylation is used on Se 2 naph to substitute either one tert-butyl Index EntryAryl selenolates apart from forming simple mononuclear complexes also form binuclear Pt complexes, in fact mononuclear and binuclear species may be in equilibrium.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Platinum Complexes of Aromatic Selenolates

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Tellurium‐Containing Heterocycles as Donor Molecules

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Theoretical Aspects of Organoselenium Chemistry

Sunoj

2011

Patai's Chemistry of Functional Groups

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The chapter offers an overview of the applications of theoretical methods in the area of organoselenium chemistry. In recent years, the availability of reliable basis sets and computational methods, especially the emergence of density functional methods, have enabled studies on increasingly complex chemical problems. A plethora of such problems in organoselenium chemistry and interesting insights on structure, properties, and reactions derived by using computational methods constitute the contents of this chapter. The types of situations described range from exotic briefly lived intermediates to structural and electronic features of stable and crystalline molecules. Properties such as nuclear magnetic resonance chemical shift and the comparison between computed and experimental quantities have been provided extensively. A number of reactions of selenium compounds with emphasis on biologically significant reactions have been highlighted. In particular, computational studies on glutathione peroxidate activity of selenium compounds have been elaborated. The electronic origins of inter‐ and intra‐molecular nonbonding interactions in organoselenium compounds and an illustration of how theoretical methods have been vital in quantifying such weak interactions have been provided.

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Peri-bridged naphthalenes from 1,8-dilithionaphthalene

Cited by 94 publications

References 0 publications

Platinum Complexes of Aromatic Selenolates

Platinum Complexes of Aromatic Selenolates

Tellurium‐Containing Heterocycles as Donor Molecules

Theoretical Aspects of Organoselenium Chemistry

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