(Z)-1,4-Diethynyl-1,4-dimethoxycyclohexa-2,5-diene has been used as a building block for the synthesis of two novel macrocycles containing buta-1,3-diyne units as bridges. The tetrayne derivative 5c has been structurally characterized by single crystal X-ray crystallographic data. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Sethuraman Sankararaman

Department Of Chemistry

Manivannan Srinivasan

Babu Varghese

1,3 butadiene derivative

1,4 DIETHYNYL 1,4 DIMETHOXYCYCLOHEXA 2,5 DIENE

alkyne derivative

BUTA 1,3 DIYNE

cyclophane derivative

macrocyclic compound

unclassified drug

article

chemical structure

Crystallization

structure analysis

synthesis

X ray crystallography

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

European Journal of Organic Chemistry

Reaction of trans-1,4-bis(trimethylsilylethynyl)cyclohexa-2,5-diene-1,4- diol with n-BuLi followed by methanesulfonyl chloride resulted in the formation of a dark red solid, which was identified as 2,5-bis(trimethylsilylethynyl) oxepin. Deprotection of the silyl groups resulted in the formation of 2,5-diethynyloxepin, a red, shock sensitive solid. Reaction of a differentially substituted cyclohexa-2,5-diene-1,4-diol gave a mixture of 2,5-diethynyl substituted oxepins. © 2005 Elsevier Ltd. All rights reserved.

Tetrahedron Letters

Synthesis of 2,5-diethynyl substituted oxepins from trans-1,4- diethynylcyclohexa-2,5-diene-1,4-diols

In the title compound, C10H8O2, the four symmetry-related molecules are connected to each other through O - H⋯O hydrogen bonds to form a helical chain along the b axis. The interconnected system is further extended along the c axis through O - H⋯O hydrogen bonds to form a two-dimensional network. Unlike its trans isomer, no C - H⋯O or C H⋯π interactions are observed in the crystal structure. © 2004 International Union of Crystallography Printed in Great Britain - all rights reserved.

Acta Crystallographica Section E: Structure Reports Online

(Z)-3,6-Diethynyl-3,6-dihydroxycyclohexa-1,4-diene

The synthesis of differentially protected/functionalized acetylenic building blocks from p-benzoquinone and their use in the synthesis of new enediynes was discussed. The diastereoisomers were separated by using column chromatography and characterized by spectroscopic data. It was found that the selective deprotection to the terminal acetylene followed by Pd(0) mediated coupling with Z-1,2-dichloroethene yielded new enediynes bearing cyclohexa-2,5-diene units.

Organic and Biomolecular Chemistry

Synthesis of differentially protected/functionalised acetylenic building blocks from p-benzoquinone and their use in the synthesis of new enediynes

Angewandte Chemie

[12.12]Paracyclophanedodecaynes C36H8 and C36Cl8: The Smallest Paracyclophynes and Their Transformation into the Carbon Cluster Ion C36−

Organic Letters

Synthesis and Structure of a New [6.6]Metacyclophane with Enediyne Bridges†

Stimulating Concepts in Chemistry

Synthesis of Novel Acetylenic Cyclophanes with Helical Chirality: Potential New Structures for Liquid Crystals

Angewandte Chemie International Edition

Acetylenic Coupling: A Powerful Tool in Molecular Construction

Synthesis of buta-1,3-diyne-bridged macrocycles with (Z)-1,4-diethynyl-1,4-dimethoxycyclohexa-2,5-diene as the building block

Journal	Data powered by TypesetEuropean Journal of Organic Chemistry
Publisher	Data powered by TypesetWiley-VCH Verlag
ISSN	1434193X
Open Access	No