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2-Bromo[6]helicene as a Key Intermediate for [6]Helicene Functionalization.

SYSNO ASEP	0488982
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	2-Bromo[6]helicene as a Key Intermediate for [6]Helicene Functionalization.
Author(s)	Jakubec, Martin (UCHP-M)_{RID, ORCID, SAI} Beránek, Tomáš (UCHP-M)_{RID, ORCID, SAI} Jakubík, Pavel (UCHP-M)_SAI Sýkora, Jan (UCHP-M)_{RID, ORCID, SAI} Žádný, Jaroslav (UCHP-M)_{RID, SAI, ORCID} Církva, Vladimír (UCHP-M)_{RID, ORCID, SAI} Storch, Jan (UCHP-M)_{RID, ORCID, SAI}
Source Title	Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263 Roč. 83, č. 7 (2018), s. 3607-3616
Number of pages	10 s.
Language	eng - English
Country	US - United States
Keywords	helicene ; racemization barrier ; enantiomers
Subject RIV	CC - Organic Chemistry
OECD category	Organic chemistry
R&D Projects	GA15-12719S GA ČR - Czech Science Foundation (CSF)
Institutional support	UCHP-M - RVO:67985858
UT WOS	000429886100018
EID SCOPUS	85045103665
DOI	10.1021/acs.joc.7b03234
Annotation	The synthesis of 2-bromo[6]helicene was revised and improved up to 51% yield. Its reactivity was thoroughly investigated, and a library of 17 different carbon, boron, nitrogen, phosphorus, oxygen and sulfur substituted derivatives was prepared. The racemization barrier for 2-bromo[6]helicene was determined, and the usage of enantiomers in the synthesis of optically pure helicenes was rationalized. The three most energy-demanding reactions using enantiomerically pure 2-bromo[6]helicene were tested in order to confirm the predicted enantiomeric excess.
Workplace	Institute of Chemical Process Fundamentals
Contact	Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227
Year of Publishing	2019

Number of the records: 1