T-Shaped Molecular Building Blocks by Combined Bridgehead and Bridge Substitution on Bicyclo[1.1.1]pentanes

KALETA, Jiří, Josef MICHL and Ctibor MAZAL. T-Shaped Molecular Building Blocks by Combined Bridgehead and Bridge Substitution on Bicyclo[1.1.1]pentanes. Journal of Organic Chemistry. 2010, vol. 75, No 7, p. 2350-2356. ISSN 0022-3263.

Basic information

• Original name: T-Shaped Molecular Building Blocks by Combined Bridgehead and Bridge Substitution on Bicyclo[1.1.1]pentanes
• Name in Czech: Molekulární stavební bloky kombinací bridgehead a bridge substituce na bicyklo[1.1.1]pentanech
• Authors: KALETA, Jiří (203 Czech Republic, belonging to the institution), Josef MICHL (840 United States of America) and Ctibor MAZAL (203 Czech Republic, guarantor, belonging to the institution).
• Edition: Journal of Organic Chemistry, 2010, 0022-3263.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10401 Organic chemistry
• Country of publisher: United States of America
• Confidentiality degree: is not subject to a state or trade secret
• WWW: URL
• Impact factor: Impact factor: 4.002
• RIV identification code: RIV/00216224:14310/10:00051340
• Organization unit: Faculty of Science
• UT WoS: 000275884400024
• Keywords (in Czech): organic synthesis;bicyclopentanes;strained compounds;molecular building blocks
• Keywords in English: organic synthesis;bicyclopentanes;strained compounds;molecular building blocks
• Tags: AKb, rivok
• Tags: International impact, Reviewed

Abstract

Derivatives of bicyclo[1.1.1]pentane differentially substituted in bridgehead (1,3) and bridge (2,4) positions have been synthesized. They represent a new T-shaped structural module consisting of a rigid rod with a nearly freely rotating side arm, possibly useful as a molecular building block in syntheses of more complex covalent or supramolecular scaffolds useful in bottom-up construction of molecular level devices or materials. For good chemical connectivity in the axial direction, carboxylates, ethynyls, and acetylsulfanyl groups were installed at the bridgeheads. Quinoxalines were attached in the transverse direction through a highly reactive alpha-diketone system located at the bridges.

Abstract (in Czech)

Derivatives of bicyclo[1.1.1]pentane differentially substituted in bridgehead (1,3) and bridge (2,4) positions have been synthesized. They represent a new T-shaped structural module consisting of a rigid rod with a nearly freely rotating side arm, possibly useful as a molecular building block in syntheses of more complex covalent or supramolecular scaffolds useful in bottom-up construction of molecular level devices or materials. For good chemical connectivity in the axial direction, carboxylates, ethynyls, and acetylsulfanyl groups were installed at the bridgeheads. Quinoxalines were attached in the transverse direction through a highly reactive alpha-diketone system located at the bridges.

Links

• ME09114, research and development project: Name: Spolupráce v oblasti energie a nanověd: USA a Evropa (Collaboration in Energy and Nanoscience)

Investor: Ministry of Education, Youth and Sports of the CR, Collaboration in Energy and Nanoscience, Research and Development Programme KONTAKT (ME)