Inclusion abilities towards hexyne isomers by co-crystallization with extended V-shaped host molecule

Kawahata, Masatoshi; Tominaga, Masahide; Fujimaru, Kousuke; Hyodo, Tadashi; Yamaguchi, Kentaro

doi:10.1016/j.tet.2019.130576

Cited by 3 publications

(4 citation statements)

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“…Jiaqi synthesized oxidative degradation catalysts characterized by low steric hindrance and high activity from 1,3-adamantanediol. Moreover, 1,3-adamantanediol is also used in the fields of molecular recognition, − drug synthesis, − and surfactants . For example, Kawahata and co-workers synthesized disubstituted adamantanes having nitrophenol moieties for efficient recognition of ketone and ester molecules.…”

Section: Introductionmentioning

confidence: 99%

“…On this basis, Tian and co-workers 31 synthesized the nitrogen− oxygen radical catalyst (1-Me-AZADO/SBA-15), which catalyzes the oxidation of secondary alcohols to ketones. Jiaqi 33 synthesized oxidative degradation catalysts characterized by low steric hindrance and high activity from 1,3adamantanediol. Moreover, 1,3-adamantanediol is also used in the fields of molecular recognition, 34−37 drug synthesis, 38−40 and surfactants.…”

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confidence: 99%

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Practical and Scalable Synthesis of 1,3-Adamantanediol

Hao,

Chen,

Yang

et al. 2024

Org. Process Res. Dev.

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A new method for the efficient synthesis of 1,3-adamantanediol is proposed. It has the advantages of good reaction selectivity, high isolated yield, easy purification, and safe operation. 3-Hydroxyadamantane-1-carboxylic acid reacts first with thionyl chloride to form 1,3-dichloro adamantane, which is then converted to 1,3-adamantanediol in a "triethylamine−water" solution. Three reaction types are involved: chlorination, decarbonylation, and hydrolysis. Under optimal reaction conditions, total isolated yields of up to 95% and purities of up to 99% were achieved. Isolated yields of 100 g per batch have been achieved, with potential for industrial production. We completed the decarbonylation of acyl chloride without the use of a metal catalyst. In addition, the reaction mechanism was investigated by combining experimental data and density functional theory.

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Section: Introductionmentioning

confidence: 99%

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confidence: 99%

Practical and Scalable Synthesis of 1,3-Adamantanediol

Hao,

Chen,

Yang

et al. 2024

Org. Process Res. Dev.

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“…Nitriles have been included in the cavities of brominated calixarenes, Klemperer’s inorganic cavitand, and a Mg-based metal–organic framework (MOF); their recognition by pillarenes was utilized to construct supramolecular polymers . Terminal alkynes were found to form complexes with urea as early as 1960, and have been included in the cavities of Rebek’s capsules and V-shaped adamantane-based hosts . In most cases, however, crystal structures were not obtained, nor was significant selectivity observed.…”

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confidence: 99%

“…15 Terminal alkynes were found to form complexes with urea as early as 1960, 16 and have been included in the cavities of Rebek's capsules 17 and V-shaped adamantanebased hosts. 18 In most cases, however, crystal structures were not obtained, nor was significant selectivity observed. In this Letter, we show that the readily synthesized cyclotetrabenzoin esters can serve as hosts for thin aliphatic nitrile and terminal alkyne guests, which engage their π-bonds through interactions with the four aromatic walls of the host cavity.…”

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confidence: 99%

Cyclobenzoin Esters as Hosts for Thin Guests

et al. 2021

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Nitriles and terminal alkynes are important compounds in industrial and academic settings. Their supramolecular binding has been challenging without the intervention of metals, because of the small dimensions of their linear-C≡N and-C≡CH groups. Using a combination of crystallography and computation, we have shown that cyclotetrabenzoin esters can host terminal triple bonds of alkynes and nitriles in their electron-poor cavities. Within these cavities, π-clouds of triple bonds can establish favorable and virtually equidistant interactions with the four aromatic walls of the cyclotetrabenzoin skeleton. Binding is selective for aliphatic nitriles and terminal alkynes, with their aromatic counterparts residing outside of the cyclotetrabenzoin cavity. These findings are of relevance in the binding, separations, and activation of these and other linear molecular guests.

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