Molecular Rods Combining o-Carborane and Bicyclo[1.1.1]pentane
Cages: An Insertion of the Triple Bond Located Next to a Highly
Strained Cage

J 2015

Molecular Rods Combining o-Carborane and Bicyclo[1.1.1]pentane Cages: An Insertion of the Triple Bond Located Next to a Highly Strained Cage

KALETA, Jiří, Zbyněk JANOUŠEK, Marek NEČAS and Ctibor MAZAL

Basic information

Original name

Molecular Rods Combining o-Carborane and Bicyclo[1.1.1]pentane Cages: An Insertion of the Triple Bond Located Next to a Highly Strained Cage

Authors

KALETA, Jiří (203 Czech Republic), Zbyněk JANOUŠEK (203 Czech Republic), Marek NEČAS (203 Czech Republic, belonging to the institution) and Ctibor MAZAL (203 Czech Republic, guarantor, belonging to the institution)

Edition

Organometallics, Spojené státy americké, American Chemical Society, Washington DC, 2015, 0276-7333

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

http://pubs.acs.org/doi/abs/10.1021/acs.organomet.5b00002

Impact factor

Impact factor: 4.186

RIV identification code

RIV/00216224:14310/15:00083775

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/acs.organomet.5b00002

UT WoS

000350841200019

Keywords in English

KeyWords Plus:DEHYDROGENATIVE ALKYNE-INSERTION; DICOBALT OCTACARBONYL; POLYBORANE REACTIONS; IONIC LIQUIDS; ROTORS; MECHANISM; ARRAYS; DECABORANE; REDUCTION

Abstract

V originále

Octacarbonyl dicobalt and bis(dimethyl sulfide)decaborane B10H12(Me2S)2 were successfully added to 1,3-diethynylbicyclo[1.1.1]pentane in good yields. This is an interesting example of a cycloaddition reaction achieved next to the bicyclopentane cage that tends to rearrange in many other cases. It proves that both reagents attack the triple bond in a more or less concerted manner that prevents the rearrangement. Products of the latter reaction are of a particular interest because the bicyclopentane and o-carborane cages are immediately linked in their rodlike structures. The new kind of molecular rotors was thus constructed. 1H and 13C nuclear magnetic resonance spectra in solution reveal an averaged rotational symmetry of the molecules with a well-defined geometry that has been confirmed by X-ray structural analysis in several examples.

Links

ED1.1.00/02.0068, research and development project

Name: CEITEC - central european institute of technology

Citovat

KALETA, Jiří, Zbyněk JANOUŠEK, Marek NEČAS and Ctibor MAZAL. Molecular Rods Combining o-Carborane and Bicyclo[1.1.1]pentane Cages: An Insertion of the Triple Bond Located Next to a Highly Strained Cage. Organometallics. Spojené státy americké: American Chemical Society, Washington DC, 2015, vol. 34, No 5, p. 967-972. ISSN 0276-7333. Available from: https://dx.doi.org/10.1021/acs.organomet.5b00002.

@article{1310471,
   author = {Kaleta, Jiří and Janoušek, Zbyněk and Nečas, Marek and Mazal, Ctibor},
   article_location = {Spojené státy americké},
   article_number = {5},
   doi = {http://dx.doi.org/10.1021/acs.organomet.5b00002},
   keywords = {KeyWords Plus:DEHYDROGENATIVE ALKYNE-INSERTION; DICOBALT OCTACARBONYL; POLYBORANE REACTIONS; IONIC LIQUIDS; ROTORS; MECHANISM; ARRAYS; DECABORANE; REDUCTION},
   language = {eng},
   issn = {0276-7333},
   journal = {Organometallics},
   title = {Molecular Rods Combining o-Carborane and Bicyclo[1.1.1]pentane Cages: An Insertion of the Triple Bond Located Next to a Highly Strained Cage},
   url = {http://pubs.acs.org/doi/abs/10.1021/acs.organomet.5b00002},
   volume = {34},
   year = {2015}
}

TY  - JOUR
ID  - 1310471
AU  - Kaleta, Jiří - Janoušek, Zbyněk - Nečas, Marek - Mazal, Ctibor
PY  - 2015
TI  - Molecular Rods Combining o-Carborane and Bicyclo[1.1.1]pentane Cages: An Insertion of the Triple Bond Located Next to a Highly Strained Cage
JF  - Organometallics
VL  - 34
IS  - 5
SP  - 967-972
EP  - 967-972
PB  - American Chemical Society, Washington DC
SN  - 02767333
KW  - KeyWords Plus:DEHYDROGENATIVE ALKYNE-INSERTION
KW  - DICOBALT OCTACARBONYL
KW  - POLYBORANE REACTIONS
KW  - IONIC LIQUIDS
KW  - ROTORS
KW  - MECHANISM
KW  - ARRAYS
KW  - DECABORANE
KW  - REDUCTION
UR  - http://pubs.acs.org/doi/abs/10.1021/acs.organomet.5b00002
L2  - http://pubs.acs.org/doi/abs/10.1021/acs.organomet.5b00002
N2  - Octacarbonyl dicobalt and bis(dimethyl sulfide)decaborane B10H12(Me2S)2 were successfully added to 1,3-diethynylbicyclo[1.1.1]pentane in good yields. This is an interesting example of a cycloaddition reaction achieved next to the bicyclopentane cage that tends to rearrange in many other cases. It proves that both reagents attack the triple bond in a more or less concerted manner that prevents the rearrangement. Products of the latter reaction are of a particular interest because the bicyclopentane and o-carborane cages are immediately linked in their rodlike structures. The new kind of molecular rotors was thus constructed. 1H and 13C nuclear magnetic resonance spectra in solution reveal an averaged rotational symmetry of the molecules with a well-defined geometry that has been confirmed by X-ray structural analysis in several examples.
ER  -

KALETA, Jiří, Zbyněk JANOUŠEK, Marek NEČAS and Ctibor MAZAL. Molecular Rods Combining o-Carborane and Bicyclo[1.1.1]pentane Cages: An Insertion of the Triple Bond Located Next to a Highly Strained Cage. \textit{Organometallics}. Spojené státy americké: American Chemical Society, Washington DC, 2015, vol.~34, No~5, p.~967-972. ISSN~0276-7333. Available from: https://dx.doi.org/10.1021/acs.organomet.5b00002.

Detailed Information on Publication Record