A New, Safe and Convenient Procedure for Reduction of Naphthalene and Anthracene: Synthesis of Tetralin in a One-Pot Reaction

Menzek, Abdullah; Altundaş, Aliye; Gültekin, Demet Demirci

doi:10.3184/030823403322863201

Cited by 16 publications

(19 citation statements)

References 18 publications

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“…High temperatures (60 -1458) have been used in the reduction of naphthalene to 1,4-dihydronaphthalene (2) since 1942 [3]. We performed the reduction of naphthalene and naphthalene derivatives with Na and t-BuOH to give the corresponding 1,4-dihydronaphthalene and naphthalene derivatives in high yields at room temperature as the sole product (Scheme 1) [4].…”

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Reductions of Benzene Derivatives Whose Benzylic Positions Bear Oxygen Atoms under Mild Conditions

Menzek

Karakaya

Kaya

2008

Helvetica Chimica Acta

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“…Reduction reactions performed at room temperature have certain advantages [4] [6]. Reduction reactions of compounds whose benzylic positions bear heteroatoms such as O-and N-atoms may be important under mild conditions.…”

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Reductions of Benzene Derivatives Whose Benzylic Positions Bear Oxygen Atoms under Mild Conditions

Menzek

Karakaya

Kaya

2008

Helvetica Chimica Acta

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“…In the current study an easy, economical, fourstep protocol for synthesis of the product 4 is announced (Figure 5). Firstly, 1,4dihydronaphthalene (8) was obtained via Birch reduction with mild conditions starting from naphthalene which is selectively reduced from the 1,4 positions, according to a method previously reported in the literature [28]. In the next step, the reaction between 1,4-dihydronaphthalene (8) and dichlorocarbene which generated in situ from CHCl3 and t-BuOK gave the previously reported the dichlorocyclopropane derivate 9 [29].…”

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An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene

Erdoğan

2021

Sakarya University Journal of Science

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Herein, a new efficient method for the synthesis of 2-bromo-3-(bromomethyl)naphthalene is reported. The synthesis is based on (1) preparation of 1,4-dihydronaphthalene via Birch reduction with mild conditions from the reaction of naphthalene, and (2) the reaction between 1,4-dihydronaphthalene and dichlorocarbene formed in situ from chloroform and potassium tert-butoxide (t-BuOK), and (3) access to the key intermediate 1H-cyclopropa[b]naphthalene from the reaction of 1,1-dichloro-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalene with t-BuOK, followed by ring-opening of the cyclopropane via bromination with molecular bromine (Br2). This synthetic sequence allows simple preparation of 2-bromo-3-(bromomethyl)naphthalene in higher yields compared to the two previously reported syntheses. The synthetic approach is modular, low cost, and rapid, and can be utilized to synthesize building blocks of naphthalene derivatives.

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“…Characterization of the white product matches that previously described. 8 4,8,11]tetraazacyclotetradecine or Dimesylatetetraazaannulene (dmtaa). A 500 mL round-bottom flask was charged with dhtaa (0.955 g, 2.36 mmol) and dry THF (250 mL).…”

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Carbon Dioxide Copolymerization Study with a Sterically Encumbering Naphthalene-Derived Oxide

Darensbourg

Kyran

2015

ACS Catal.

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Poly(1,4-dihydronaphthalene carbonate) has been prepared via the catalytic coupling of carbon dioxide and 1,4-dihydronaphthalene oxide using chromium(III) catalysts. The copolymer formation is found to be greatly dependent on the steric environment around the metal center. Traditional (salen)Cr III X/cocatalyst systems bearing bulky tbutyl groups hinder the approach of the large monomer, significantly diminishing polymer chain growth and providing the entropically favored cyclic byproduct in excess. In contrast, employing the sterically unencumbered azaannulene-derived catalyst, (tmtaa)Cr III X/cocatalyst system (tmtaa = tetramethyltetraazaannulene) shows polymer selectivity close to 90% with three times the activity (TOF = 20−30 h −1 ). With the use of a bifunctional (salen)Cr III catalyst, even higher polymer selectivity (>90%) can be observed. The complete synthesis of a new bifunctional tetraazaannulene ligand for a more effective catalyst is also described herein.

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A New, Safe and Convenient Procedure for Reduction of Naphthalene and Anthracene: Synthesis of Tetralin in a One-Pot Reaction

Cited by 16 publications

References 18 publications

Reductions of Benzene Derivatives Whose Benzylic Positions Bear Oxygen Atoms under Mild Conditions

Reductions of Benzene Derivatives Whose Benzylic Positions Bear Oxygen Atoms under Mild Conditions

An efficient synthetic approach for the transition metal-free preparation of 2-bromo-3-(bromomethyl)naphthalene from naphthalene

Carbon Dioxide Copolymerization Study with a Sterically Encumbering Naphthalene-Derived Oxide

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