New evidence for and new reactions of ortho-lithio ylides

Although a-lithio ylide Ph3P+C-HBr was generated from [Ph3PCH2Br]Br through halogen-metal exchange, the reaction of Ph3P+C-H2 with Me3CLi or Me2CHCH2Li produces the o-lithio ylide I nearly quant. I is stable at -60 Deg but slowly decomps. at higher temps. via a cyclization product II to give the a-lithio phosphole III, as shown by 1H NMR. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 26, 13, 1623-6
Year:
1985
Keywords:
Note:
CAN 103:178328
29-7
Organometallic and Organometalloidal Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4039
written in English.
3487-44-3 Role: RCT (Reactant), RACT (Reactant or reagent) (NMR spectrum and methylation of); 1486-28-8P; 16546-79-5P Role: FORM (Formation, nonpreparative), PREP (Preparation) (formation of, by hydrolysis of lithiated phosphol); 98775-37-2P Role: PREP (Preparation) (formation, NMR spectrum, and rearrangement of); 1034-49-7 Role: RCT (Reactant), RACT (Reactant or reagent) (lithiation of); 98753-65-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrolysis of); 2065-66-9P; 4736-60-1P; 24470-78-8P; 93746-57-7P; 93746-58-8P; 98753-64-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 82537-28-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn., NMR spectrum, and methylation of); 93746-77-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn., NMR spectrum, and reactions of)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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