Elimination of β-thioalkoxy alcohols under Mitsunobu conditions. A new synthesis of conjugated enynes from propargylic dithioacetals
Journal
Journal of Organic Chemistry
Journal Volume
73
Journal Issue
21
Pages
8357-8363
Date Issued
2008
Author(s)
Chen C.-W
Abstract
(Chemical Equation Presented) Treatment of propargylic dithiolanes 1 with nBuLi followed by a carbonyl electrophile yields the corresponding homopropargylic alcohol 3. Upon treatment with 2 equiv of PPh3 and DIAD, elimination of SR and OH moieties from 3 affords the corresponding olefins 4 in moderate to good yield. The reaction can be considered an alternative of McMurry coupling of two different carbonyl equivalents. © 2008 American Chemical Society.
SDGs
Other Subjects
Carbonylation; Chemical reactions; Olefins; Chemical equations; Conjugated enynes; Dithioacetals; Dithiolanes; Electrophile; Good yields; Homopropargylic alcohols; Mitsunobu conditions; Synthesis of; Organic polymers; acetal derivative; alcohol derivative; alkene derivative; carbonyl derivative; thiol derivative; article; chemical reaction; chemical structure; elimination reaction; Mitsunobu reaction; quantum yield; reaction analysis; stereospecificity; synthesis
Type
journal article