title: 3-Chloro-1-lithiopropene, a functional organolithium reagent, and its reactions with alkylboronates to give 3-alkylprop-1-en-3-ols.
abstract: The reagent 3-chloro-1-lithiopropene (4) can be generated by treating 1-bromo-3-chloropropene with t-BuLi. It is unstable but if generated at low temperature in the presence of alkylboronic esters, such as 3, is trapped in situ to give rearrangement products 2, which on oxidation give 3-alkylprop-1-en-3-ols in good yields. The reaction works for primary, secondary, benzylic, and even tertiary alkylboronic esters, providing allylic alcohols bearing almost any alkyl group available using organoborane chemistry and incorporating all features of such groups.
authors.affiliation: School of Chemistry, Cardiff University , Main Building, Park Place, Cardiff CF10 3AT, United Kingdom.
authors.forename: Keith
authors.initials: K
authors.lastname: Smith
authors.forename: Mark C
authors.initials: MC
authors.lastname: Elliott
authors.forename: D Heulyn
authors.initials: DH
authors.lastname: Jones
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D056831:Coordination Complexes / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: C586630:3-chloro-1-lithiopropene; D000438:Alcohols; D001897:Boronic Acids; D056831:Coordination Complexes; D009942:Organometallic Compounds
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