What is it about?
This study describes a new reaction in which 1-chlorovinyl p-tolyl sulfoxides react consecutively with [chloro(p-tolylsulfinyl)methyl]lithium to produce highly functionalized methylenecyclopropanes. These strained three-membered ring compounds can then be converted into valuable conjugated enynes by treatment with butyllithium. The work demonstrates an efficient strategy for constructing complex molecular frameworks from readily available sulfoxide precursors.
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Why is it important?
Methylenecyclopropanes are versatile synthetic intermediates because their strained ring structures undergo unique chemical transformations. This work introduces a previously unknown consecutive reaction that efficiently creates multifunctionalized methylenecyclopropanes. The resulting compounds can be further transformed into conjugated enynes, providing a new route to structurally diverse molecules that may be useful in synthetic organic chemistry.
Perspectives
This work began with an unexpected observation: 1-chlorovinyl p-tolyl sulfoxides reacted with two equivalents of a carbon nucleophile to afford multifunctionalized methylenecyclopropanes through an unprecedented consecutive reaction. We also found that these strained products could be readily converted into conjugated enynes by ring-opening. We look forward to discovering further unusual reactions of 1-chlorovinyl p-tolyl sulfoxides and expanding their applications in organic synthesis.
Associate Professor Tsutomu Kimura
Read the Original
This page is a summary of: Consecutive reaction of 1-chlorovinyl p-tolyl sulfoxides with [chloro(p-tolylsulfinyl)methyl]lithium leading to the formation of multi-functionalized methylenecyclopropanes, Tetrahedron Letters, September 2017, Elsevier,
DOI: 10.1016/j.tetlet.2017.07.083.
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