1,3-Dilithio-2-(diphenylmethylene)propane

Tetrahedron Letters

Volumn 49, Issue 35, 2008, Pages 5182-5185

  Lillo, Victor J ^a   Gómez, Cecilia ^a   Yus, Miguel ^a  

^a Departamento de Química Orgánica   (Spain)

Author keywords

1,3 Dilithiopropane derivative; Aliphatic SE reaction; Cyclopropane ring opening; DTBB catalysed lithiation; Lithium

Indexed keywords

1,3 DILITHIO 2 (DIPHENYLMETHYLENE)PROPANE; 2,2 DIPHENYLMETHYLENECYCLOPROPANE; 3 CHLORO 2 (CHLOROMETHYL)PROPENE; 4,4' BIS(TERT BUTYLBIPHENYL); ALKENE DERIVATIVE; BIPHENYL DERIVATIVE; CYCLOPROPANE DERIVATIVE; LITHIUM; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; HYDROLYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 47149095919     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.065     Document Type: Article

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57. 11 gave the same reaction products but much slower. For instance, by using water as the electrophile, total conversion was achieved after 3 h in the presence of naphthalene, whereas only ca. 30% conversion was observed in its absence.
58. One referee suggested that intermediate 6 (Scheme 2) could also be generated from intermediate 11 through a different β-elimination process as follows:{A figure is presented}We thank the referee for this interesting suggestion.
59. The same process at room temperature gave the same results but with poorer yield, and the reaction crude was not clean. Under these conditions a proton abstraction from the solvent decomposed partially the lithiated intermediates (see Ref. 13).