Preparation of Azulenes Substituted at Seven-Membered Cycle with 2- and 3-thiophenevinyl Groups<br>

Birzan, Liviu; Tecuceanu, Victorita; Draghici, Constantin C.; Hanganu, Anamaria; Razus, Alexandru C.

Liviu Birzan, Victorita Tecuceanu, Constantin C. Draghici, Anamaria Hanganu, Alexandru C. Razus

Preparation of Azulenes Substituted at Seven-Membered Cycle with 2- and 3-thiophenevinyl Groups

Abstract:

This paper comes as a continuation of our efforts to prepare vinylazulenes, moving our attention to the seven-membered azulene cycle. Several azulenic substrates were tested in order to study the possibility of preparation of poly(thiophenevinyl)azulenes, needed for the generation of dendrimeric structures. The compounds containing methyls in positions 4,6 and 8 could be condensed with 2- and 3- thiophenecarbaldehyde in tBuOK/THF yielding mono-, bis- and tris- condensed products in function of molar ratio of reagents, catalyst, solvent. The reaction works in thermodynamic control, preferring 6-position instead of 4(8)-position, which generates less stable alkenes (steric hindrance) and has a trans stereochemistry. Usually mixtures of products are obtained if more condensation position are present, even if a large aldehyde excess is used. In forcing conditions, the intermediate alcohols suffer an Oppenauer hydride transfer to the excess aldehyde, generating undesired ketones. For condensation of a methyl group situated on the five-membered cycle it must be activated by substitution with +PPh3 followed by a Wittig condensation.

Keywords:
thiophenevinylazulenes; condensations; Wittig; H-NMR; UV-Vis spectra

Issue: 2020, Volume 71, Issue 7

Pages: 212-224

Publication date: 2020/8/4

https://doi.org/10.37358/RC.20.7.8239

Download Pdf Article

This article is published under the Creative Commons Attribution 4.0 International License

Citation Styles

Cite this article as:
BIRZAN, L., TECUCEANU, V., DRAGHICI, C.C., HANGANU, A., RAZUS, A.C., Preparation of Azulenes Substituted at Seven-Membered Cycle with 2- and 3-thiophenevinyl Groups
, Rev. Chim., 71(7), 2020, 212-224.

Vancouver
Birzan L, Tecuceanu V, Draghici CC, Hanganu A, Razus AC. Preparation of Azulenes Substituted at Seven-Membered Cycle with 2- and 3-thiophenevinyl Groups
. Rev. Chim.[internet]. 2020 Jul;71(7):212-224. Available from: https://doi.org/10.37358/RC.20.7.8239

APA 6th edition
Birzan, L., Tecuceanu, V., Draghici, C.C., Hanganu, A. & Razus, A.C. (2020). Preparation of Azulenes Substituted at Seven-Membered Cycle with 2- and 3-thiophenevinyl Groups
. Revista de Chimie, 71(7), 212-224. https://doi.org/10.37358/RC.20.7.8239

Harvard
Birzan, L., Tecuceanu, V., Draghici, C.C., Hanganu, A., Razus, A.C. (2020). 'Preparation of Azulenes Substituted at Seven-Membered Cycle with 2- and 3-thiophenevinyl Groups
', Revista de Chimie, 71(7), pp. 212-224. https://doi.org/10.37358/RC.20.7.8239

IEEE
L. Birzan, V. Tecuceanu, C.C. Draghici, A. Hanganu, A.C. Razus, "Preparation of Azulenes Substituted at Seven-Membered Cycle with 2- and 3-thiophenevinyl Groups
". Revista de Chimie, vol. 71, no. 7, pp. 212-224, 2020. [online]. https://doi.org/10.37358/RC.20.7.8239

Text
Liviu Birzan, Victorita Tecuceanu, Constantin C. Draghici, Anamaria Hanganu, Alexandru C. Razus,
Preparation of Azulenes Substituted at Seven-Membered Cycle with 2- and 3-thiophenevinyl Groups
,
Revista de Chimie,
Volume 71, Issue 7,
2020,
Pages 212-224,
ISSN 2668-8212,
https://doi.org/10.37358/RC.20.7.8239.
(https://revistadechimie.ro/Articles.asp?ID=8239)
Keywords: thiophenevinylazulenes; condensations; Wittig; H-NMR; UV-Vis spectra

RIS
TY - JOUR
T1 - Preparation of Azulenes Substituted at Seven-Membered Cycle with 2- and 3-thiophenevinyl Groups

A1 - Birzan, Liviu
A2 - Tecuceanu, Victorita
A3 - Draghici, Constantin C.
A4 - Hanganu, Anamaria
A5 - Razus, Alexandru C.
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2020
VL - 71
IS - 7
SP - 212
EP - 224
UR - https://doi.org/10.37358/RC.20.7.8239
KW - thiophenevinylazulenes
KW - condensations
KW - Wittig
KW - H-NMR
KW - UV-Vis spectra
ER -

BibTex
@article{RevCh2020P212,
author = {Birzan Liviu and Tecuceanu Victorita and Draghici Constantin C. and Hanganu Anamaria and Razus Alexandru C.},
title = {Preparation of Azulenes Substituted at Seven-Membered Cycle with 2- and 3-thiophenevinyl Groups
},
journal = {Revista de Chimie},
volume = {71},
number = {7},
pages = {212-224},
year = {2020},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.20.7.8239},
url = {https://revistadechimie.ro/Articles.asp?ID=8239}
}

<<<< back

PUBLISHING SECTION

Author Guidelines

* Paper Drafting

* Paper Template

* Ethical Statement

* Paper Submission

Ghidul Autorului (ro)

Open Access & Archiving Policy

Search Authors

LATEST NEWS
	NUMAR OMAGIAL PETRU PONI.. detalii
	Revista de Chimie - 70 de ani de aparitie neintrerupta.. detalii
	English-Romanian Dictionary for Mechanical Engineering (download pdf)