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.

Sethuraman Sankararaman

Department Of Chemistry

Manivannan Srinivasan

Addition reactions

column chromatography

Isomers

Mixtures

Synthesis (chemical)

DIASTEREOMERIC MIXTURES

Aromatic compounds

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

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IIT Madras

Organic and Biomolecular 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

(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.

European Journal of Organic Chemistry

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

Physics Today

Atmospheric oxygen may have been present earlier than expected

Chemical Communications

Carbon-rich acetylenic scaffolding: rods, rings and switches

Stimulating Concepts in Chemistry

Protective Groups in Organic Synthesis

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

Journal	Organic and Biomolecular Chemistry
ISSN	14770520
Open Access	No