1,3-Diethynylbicyclo[1.1.1]pentane, a Useful Molecular Building
Block

J 2012

1,3-Diethynylbicyclo[1.1.1]pentane, a Useful Molecular Building Block

KALETA, Jiří, Marek NEČAS a Ctibor MAZAL

Základní údaje

Originální název

1,3-Diethynylbicyclo[1.1.1]pentane, a Useful Molecular Building Block

Autoři

KALETA, Jiří (203 Česká republika, domácí), Marek NEČAS (203 Česká republika, domácí) a Ctibor MAZAL (203 Česká republika, garant, domácí)

Vydání

European Journal of Organic Chemistry, 2012, 1434-193X

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 3.344

Kód RIV

RIV/00216224:14310/12:00064414

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1002/ejoc.201200351

UT WoS

000307937800014

Klíčová slova anglicky

Alkynes; Cross coupling; Umpolung; Small ring systems; Rod-like molecules

Štítky

AKR, rivok

Změněno: 8. 2. 2018 12:13, doc. RNDr. Ctibor Mazal, CSc.

Anotace

V originále

1,3-Diethynylbicyclo[1.1.1]pentane (DEBCP) has been found to be a valuable molecular building block mostly for the synthesis of extended, rigid, rod-like molecules. With its straightforward linear geometry, DEBCP can be used as a nonconjugated alternative to more frequently used pi-conjugated, rod-like building blocks. Examples of reactions that introduce DEBCP into larger structures are (1) the reaction of DEBCP lithium acetylides with electrophiles such as TMSCl, CO2, and Ph2PCl, (2) Sonogashira–Hagihara cross-coupling reactions with aryl or heteroaryl iodides or bromides, and (3) umpolung reactions that afford the corresponding dibromo and diiodo derivatives of DEBCP, which then successfully react with tert-C-cuprates derived from p- and m-dicarbadodecaboranes or bicyclopentanes. These umpolung reactions afforded a new class of molecular rods that combine carborane or bicyclo[1.1.1]pentane cages with ethynylene linkers. Many of the DEBCP derivatives were studied by single-crystal X-ray diffraction. They form well-organized arrays of molecular rotors, the DEBCP units, and so can be considered as examples of artificial molecular-size machines.

Návaznosti

ED1.1.00/02.0068, projekt VaV

Název: CEITEC - central european institute of technology

MSM0021622410, záměr

Název: Fyzikální a chemické vlastnosti pokročilých materiálů a struktur

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Fyzikální a chemické vlastnosti pokročilých materiálů a struktur

Citovat

KALETA, Jiří, Marek NEČAS a Ctibor MAZAL. 1,3-Diethynylbicyclo[1.1.1]pentane, a Useful Molecular Building Block. European Journal of Organic Chemistry. 2012, roč. 2012, č. 25, s. 4783-4796. ISSN 1434-193X. Dostupné z: https://dx.doi.org/10.1002/ejoc.201200351.

@article{1092098,
   author = {Kaleta, Jiří and Nečas, Marek and Mazal, Ctibor},
   article_number = {25},
   doi = {http://dx.doi.org/10.1002/ejoc.201200351},
   keywords = {Alkynes; Cross coupling; Umpolung; Small ring systems; Rod-like molecules},
   language = {eng},
   issn = {1434-193X},
   journal = {European Journal of Organic Chemistry},
   title = {1,3-Diethynylbicyclo[1.1.1]pentane, a Useful Molecular Building Block},
   url = {http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201200351/full},
   volume = {2012},
   year = {2012}
}

TY  - JOUR
ID  - 1092098
AU  - Kaleta, Jiří - Nečas, Marek - Mazal, Ctibor
PY  - 2012
TI  - 1,3-Diethynylbicyclo[1.1.1]pentane, a Useful Molecular Building Block
JF  - European Journal of Organic Chemistry
VL  - 2012
IS  - 25
SP  - 4783-4796
EP  - 4783-4796
SN  - 1434193X
KW  - Alkynes
KW  - Cross coupling
KW  - Umpolung
KW  - Small ring systems
KW  - Rod-like molecules
UR  - http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201200351/full
L2  - http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201200351/full
N2  - 1,3-Diethynylbicyclo[1.1.1]pentane (DEBCP) has been found to be a valuable molecular building block mostly for the synthesis of extended, rigid, rod-like molecules. With its straightforward linear geometry, DEBCP can be used as a nonconjugated alternative to more frequently used pi-conjugated, rod-like building blocks. Examples of reactions that introduce DEBCP into larger structures are (1) the reaction of DEBCP lithium acetylides with electrophiles such as TMSCl, CO2, and Ph2PCl, (2) Sonogashira–Hagihara cross-coupling reactions with aryl or heteroaryl iodides or bromides, and (3) umpolung reactions that afford the corresponding dibromo and diiodo derivatives of DEBCP, which then successfully react with tert-C-cuprates derived from p- and m-dicarbadodecaboranes or bicyclopentanes. These umpolung reactions afforded a new class of molecular rods that combine carborane or bicyclo[1.1.1]pentane cages with ethynylene linkers. Many of the DEBCP derivatives were studied by single-crystal X-ray diffraction. They form well-organized arrays of molecular rotors, the DEBCP units, and so can be considered as examples of artificial molecular-size machines.
ER  -

KALETA, Jiří, Marek NEČAS a Ctibor MAZAL. 1,3-Diethynylbicyclo[1.1.1]pentane, a Useful Molecular Building Block. \textit{European Journal of Organic Chemistry}. 2012, roč.~2012, č.~25, s.~4783-4796. ISSN~1434-193X. Dostupné z: https://dx.doi.org/10.1002/ejoc.201200351.

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