A Simple and Economical Synthetic Route to p-Ethynylaniline and Ethynyl-Terminated Substrates

Melissaris, Anastasios P.; Litt, Morton H.

doi:10.1021/jo00098a051

Cited by 59 publications

(29 citation statements)

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“…Although the 2-hydroxypropyl groups were attractive in consideration of separation, the deprotection reaction always required harsh conditions (e.g., strong base, high temperature, and a long reaction time) [21][22][23]. Furthermore, for molecules bearing more than one 2-hydroxypropyl group, the deprotection yields were often low or long reaction time was required [24][25][26]. Compound 1 was obtained in only 10% yield when 3a was treated with NaOH in toluene under reflux for 8 h (Table 3, entry 1).…”

Section: Resultsmentioning

confidence: 99%

A simple and efficient synthesis of 1,3,5-tris[2-(3,5-diethynylphenyl)ethynyl]benzene from 1,3,5-triethynylbenzene

Huang

2011

Res Chem Intermed

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A concise and convenient three-step process is reported for preparation of 1,3,5-tris[2-(3,5-diethynylphenyl)ethynyl]benzene from 1,3,5-triethynylbenzene and 2-hydroxypropyl group-protected peripheral monomers via a Sonogashira coupling-deprotection reaction sequence. This approach had several advantages, for example high yields, short reaction time, and simple separation procedure. In the key step a modified Sonogashira reaction was developed, under which conditions the coupling of 1,3,5-triethynylbenzene and substituted iodobenzenes proceeded rapidly, giving the desired products in good to excellent yields.

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Section: Resultsmentioning

confidence: 99%

A simple and efficient synthesis of 1,3,5-tris[2-(3,5-diethynylphenyl)ethynyl]benzene from 1,3,5-triethynylbenzene

Huang

2011

Res Chem Intermed

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“…在 B 1 的合成中, 引入端炔保护基的化学试剂通常有三甲基硅炔, 三异丙基硅炔等三烷基硅炔和 2-甲基-3-丁炔-2-醇, 前者的价格十分昂贵, 而 2-甲基-3-丁炔-2-醇的价格却十分便宜. 但在 Sonogashira 偶联反应中, 2-甲基-3-丁炔-2-醇的使用并不普遍, 原因是在经过 2-甲基-3-丁炔-2-醇引入端炔基后, 其随后的脱去 2-羟基-2-丙基制备端炔氢的反应条件十分苛刻, 通常需要强碱、高温以及长时间 [20,21] 的反应, 因而极易引起其它副反应发生, 导致 …”

Section: 苯乙炔树枝状化合物 B 1 的合成unclassified

Synthesis of Novel Phenylacetylene Dendrimers Containing Different Protective Groups for Their Terminal Acetylenes

Chen¹,

Huang²

2013

Chin. J. Org. Chem.

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“…Synthesis of the esters 4 and thioesters 5 is shown in scheme 1 An attempt at a direct coupling of 1-heptyne (11) with 4-bromobenzoic acid gave a mixture of compounds, but a coupling with the ester 13 gave the alkynyl ester 15 in a good yield [13,14]. Hydrolysis of this ester gave the desired acid 17.…”

Section: Synthesismentioning

confidence: 99%

“…1 H NMR 8.04 (d, 2, J58.63, ArH ortho to CO 2 H), 7.50 (d, 2, J58.50, ArH ortho to alkyne), 2.46 (t, 2, J57.04, a-CH 2 ), 1.63-1.59 (m, 2, b-CH 2 ), 1.42-1.38 (m, 4, 2 CH 2 ) and 0.95 (t, 3, J56.92, CH 3 ). 13 5.2.5. Preparation of the esters 4 and thioesters 5.…”

Section: Ethyl 4-heptynylbenzoate 15mentioning

confidence: 99%

The effect on mesomorphic properties of a triple bond in a terminal chain of 4,4′‐disubstituted phenyl benzoates and phenyl thiobenzoates

et al. 2005

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2005) The effect on mesomorphic properties of a triple bond in a terminal chain of 4,4′-disubstituted phenyl benzoates and phenyl thiobenzoates, Liquid Crystals, 32:2, 247-266,The effect of a triple bond in a terminal chain on the mesomorphic properties of rod-like mesogens was studied by replacing a straight alkyl chain with a terminal 1,2-alkynyl chain in some esters and thioesters of the type: or by incorporating the triple bond into an alkyl ester chain in esters and thioesters of the types:The triple bond should provide increased rigidity to the triple bond region but increased flexibility at the adjacent single bond. These should have opposite effects on the mesomorphic properties. The first compounds were synthesized by esterification of the appropriate alkynylbenzoic acids with various phenols or thiols using the carbodiimide method. Detailed syntheses are provided for the alkynylbenzoic acids. Preparation of the alkynyl ester compounds was by acylation of the precursor hydroxyl esters or thioesters using either the acid chloride or carbodiimide method. The synthesis of the phenolic or thiolic ester intermediates, usually using a protection group, is described. Mesomorphic properties of these new esters and thioesters were determined using hot stage polarizing microscopy and DSC and compared with those for the known parent compounds. Fewer mesophases having shorter temperature ranges and lower transition temperatures were usually observed. Some of the intermediate phenols or benzyl ethers were also studied. Long chain benzyloxy esters showed a nematic phase as did some of the hydroxy thioesters but no mesophases were observed in the hydroxy esters.

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A Simple and Economical Synthetic Route to p-Ethynylaniline and Ethynyl-Terminated Substrates

Cited by 59 publications

References 0 publications

A simple and efficient synthesis of 1,3,5-tris[2-(3,5-diethynylphenyl)ethynyl]benzene from 1,3,5-triethynylbenzene

A simple and efficient synthesis of 1,3,5-tris[2-(3,5-diethynylphenyl)ethynyl]benzene from 1,3,5-triethynylbenzene

Synthesis of Novel Phenylacetylene Dendrimers Containing Different Protective Groups for Their Terminal Acetylenes

The effect on mesomorphic properties of a triple bond in a terminal chain of 4,4′‐disubstituted phenyl benzoates and phenyl thiobenzoates

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