Events The 10th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 10th International Electronic Conference on Synthetic Organic Chemistry

Published date

30 Nov, 2006

Citation

Abdeslam Abou, Francisco Foubelo, Miguel Yus, Chemoselective lithiation of 6-chloro-1-halohex-1-ynes with lithium/naphthalene, in Proceedings of The 10th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2006, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-10-01400

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Chemoselective lithiation of 6-chloro-1-halohex-1-ynes with lithium/naphthalene

Abdeslam Abou ¹

Francisco Foubelo ¹

Miguel Yus ¹

1. Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante (Spain)

Abstract

The reaction of different 6-chloro-1-halohex-1-ynes (1) with lithium naphthalene (1:2 molar ratio) and a carbonyl compound R¹R²CO in THF at –78°C leads, after hydrolysis with water, to the corresponding chlorinated alcohols 2 through a selective lithiation of the sp carbon-halogen bond. The DTBB-catalysed lithiation of 6-chloro-1-halohexynes (1) in the presence of an excess of a carbonyl compound R¹R²YCO as electrophile in THF at -78 ºC led, after hydrolysis with water, to diols 3.

Keywords

DTBB-catalysed lithiation

lithium-naphthalene

bromine-lithium exchange

chlorine-lithium exchange

electrophilic substitution

diols

Modified Clemmensen reduction of some diaryl ketones with non-amalgamated zinc

Synthesis and Photochemistry of 1-iodocyclohexene: Influence of Ultrasound on Ionic vs. Radical Behaviour