Reactivity of the 1-hydropyrenyl anion towards α,ω-dibromoalkanes

DOI: 10.1039/P29950001489

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1489 - 1496 (1995)

Update date:2022-08-17

Topics:

Authors:

Dijk, Joost T. M. van

Lugtenburg, Johan

Cornelisse, Jan

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P29950001489

The reactivity of the 1-hydropyrenyl mono-anion (1^-) towards 1,2-dibromoethane, 1,3-dibromopropane and 1,4-dibromobutane has been examined.Six novel products were isolated from these reactions and characterised: spiro (2), 1,3a-dihydro-1,3a-ethanopyrene (3), 9,10,11, 11a-tetrahydro-8bH-cyclopentapyrene (4), 2,3,3a,12a-tetrahydro-1H-cyclopentapyrene (5), 3a-(3-bromopropyl)-3,3a-dihydropyrene (6) and 8b,9,10,11,12,12a-hexahydrobenzolpyrene (7).The formation of these products could be rationalised by initial attack of the dibromoalkane at positions 3a and 5 of 1^-.Deprotonation of the initial ω-bromoalkyldihydropyrenes leads to intramolecular alkylation, the course of which depends on the length of the alkyl chain.Attempts to aromatize the products resulted, except in the case of 5, in the fully aromatic pyrene derivatives cyclopentapyrene, benzopyrene, pyrene and the new cyclopenta-fused pyrene derivative, 10,11-dihydro-9H-cyclopentapyrene (9).

Full text of DOI:10.1039/P29950001489

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:Pyrene

Cas No:129-00-0

R&D Labs maybe for 129-00-0

WUHAN RISON TRADING CO.,LTD

Contact:0086-27-83607103/83642615

Address:No.498, Jianshe Ave, Wuhan, China
EGBERT CORPORATION

Contact:+86 18616952870

Address:Area
MTT Pharma & Bio-technology Co.,Ltd(expird)

Contact:+86-21-58407925

Address:Room2019, Building C, Tomson Center, No.158, Zhang Yang Road, Shanghai, China
CHEMINN LTD.

website:http://www.cheminn.com/

Contact:86-531-67875205

Address:No.9-2,South of Shanda Road, Jinan ,China
Chemtrade International ( China )

Contact:+86-532-86893005

Address:Rm 2-501, Huaxia Zonghe Building, No. 410 JInggangshan Road, Huangdao

Relevant to this article

Synthesis of novel N-carbohydrate-derived heterocyclic compounds by nucleophilic substitution reaction of carbohydrate imidazole-1-sulfonates

Doi:10.1080/07328303.2011.605193
(2011)
Co(II)-MOF: A Highly Efficient Organic Oxidation Catalyst with Open Metal Sites

Doi:10.1021/acs.inorgchem.5b01938
(2015)
Self-Assembled Cofacial Zinc–Porphyrin Supramolecular Nanocapsules as Tuneable ¹O₂ Photosensitizers

Doi:10.1002/chem.201705531
(2018)
Doi:10.1039/jr9430000326
(1943)
New turn on fluorimetric sensor for direct detection of ultra-trace ferric ions in industrial wastewater and its application by test strips

Doi:10.1016/j.jphotochem.2021.113218
(2021)
On the palladium(II)-catalysed oxidative rearrangement of propargylic acetates

Doi:10.1002/adsc.200303200
(2004)

Article Doi