A Search for Unambiguous Vinylic SRN1 Reactions

Annunziata, Alfonso; Galli, Carlo; Gentili, Patrizia; Guarnieri, Alessandra; Beit-Yannai, Michal; Rappoport, Zvi

doi:10.1002/1099-0690(200207)2002:13<2136::aid-ejoc2136>3.0.co;2-8

Cited by 15 publications

(27 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to the previous study on the syntheses of DPh1 and MPh1 , we modified the synthetic route to obtain optically active dimer compounds. A bromide of compound 1 was converted to a boronate ester to obtain compound 2 in 97 % isolated yield. Compound 2 was readily used in the Suzuki–Miyaura coupling (Scheme ).…”

Section: Methodsmentioning

confidence: 99%

Optically Active Phenylethene Dimers Based on Planar Chiral Tetrasubstituted [2.2]Paracyclophane

Gon

Morisaki

Chujo

2017

Chemistry A European J

View full text Add to dashboard Cite

Optically active phenylethene dimers based on a planar chiral 4,7,12,15-tetrasubstituted [2.2]paracyclophane were synthesized. We succeeded in controlling the molecular motion by binding luminophores in close proximity with the [2.2]paracyclophane scaffold. For example, aggregation-induced emission (AIE)-active luminophores were converted to show intense photoluminescence (PL) even in a diluted solution at room temperature and the resulting compound worked as a single-molecule thermoresponsible material around room temperature. Because of the AIE-active unit, the molecular motion could be easily activated by heating, leading to variable and reversible PL intensity. Furthermore, the π-conjugated systems with the planar chirality of 4,7,12,15-tetrasubstituted [2.2]paracyclophane provided excellent characteristics on circular dichroism (CD) and circularly polarized luminescence (CPL). The obtained dimers showed high CPL performances both in a diluted solution and in an aggregation state. We succeeded in proving that simple molecular designs composed of only carbon and hydrogen atoms could create versatile optical functionalities.

show abstract

Section: Methodsmentioning

confidence: 99%

Optically Active Phenylethene Dimers Based on Planar Chiral Tetrasubstituted [2.2]Paracyclophane

Gon

Morisaki

Chujo

2017

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…(2-Bromoethene-1,1-diyl)dibenzene (20), 33 Larger-scale procedure for aerobic oxidative dibromination of trans-stilbene (8) with HBr/air/NaNO 2 (cat.) system 5.0 mmol (901 mg) of 8 was mixed with 10 mL of freshly distilled acetonitrile, then 10.0 mmol of a 48% aqueous solution of HBr (1.13 mL) and 70 mL of a 3.6 M aqueous solution of NaNO 2 (0.25 mol of NaNO 2 ) were added.…”

Section: Trans-12-dibromo-12-dihydroacenaphthylene (12)mentioning

confidence: 99%

Selective aerobic oxidative dibromination of alkenes with aqueous HBr and sodium nitrite as a catalyst

et al. 2009

View full text Add to dashboard Cite

Various alkenes (internal, terminal, aryl and alkyl substituted) and 1,2-diphenylethyne were efficiently and selectively dibrominated using 2 equivalents of 48% aqueous hydrobromic acid, with air as an oxidant and sodium nitrite as a catalyst. Despite the presence of water, only trans dibromination occurred producing anti-1,2-dibromoalkanes and (E)-1,2-dibromo-1,2diphenylethene. A comparison of resource demand, waste production and environmental, health and safety issues of the NaNO 2 catalyzed aerobic bromination with molecular bromine and other oxidative bromination methods revealed that the proposed method is not only selective and effective but has a better environmental profile.

show abstract

“…66). The same substrate, however, affords the substitution product derived from the elimination/addition route when a carbanion is employed [145]. A mechanistic study was undertaken on the coupling of vinyl radicals with nucleophiles ((EtO) 2 PO -, -CH 2 COBu-t, and PhS -ions) and the competing H-atom abstraction reactions from various solvents (MeCN, DMSO) [146].…”

Section: Vinyl Halidesmentioning

confidence: 99%

Strategies in Synthetic Radical Organic Chemistry. Recent Advances on Cyclization and SRN1 Reactions

Rossi¹,

Peñéñory

2006

COS

View full text Add to dashboard Cite

A Search for Unambiguous Vinylic SRN1 Reactions

Cited by 15 publications

References 11 publications

Optically Active Phenylethene Dimers Based on Planar Chiral Tetrasubstituted [2.2]Paracyclophane

Optically Active Phenylethene Dimers Based on Planar Chiral Tetrasubstituted [2.2]Paracyclophane

Selective aerobic oxidative dibromination of alkenes with aqueous HBr and sodium nitrite as a catalyst

Strategies in Synthetic Radical Organic Chemistry. Recent Advances on Cyclization and SRN1 Reactions

Contact Info

Product

Resources

About