Should anionised benzylic sulfones be considered as carbenoids?

Tetrahedron Letters

Volumn 43, Issue 44, 2002, Pages 7907-7911

  Jolivet, B ^a   Uguen, D ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; CARBENOID; SOLVENT; STILBENE DERIVATIVE; SULFONE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DECOMPOSITION; REDUCTION;

EID: 0037190867     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01908-1     Document Type: Article

References (28)

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27. a of the parent methoxymethyl phenylsulfone is in the same range as those of related alkyl phenylsulfones (1a is considerably more acidic than t-butyl methylether) and the anion derived from this alkoxysulfone should, accordingly, be structurally related to any sulfone anion, with extensive delocalisation of the negative charge onto the sulfur atom.
28. A similar result is obtained by decomposing the lithio derivative of benzyl chloride in the presence of cyclohexene (Ref. 13b, chapter V). It is interesting to note that the thermal decomposition of the lithio derivative of benzaldehyde tosylhydrazone (Kabalka, G. W.; Wu, Z.; Ju, Y. Tetrahedron Lett. 2001, 42, 4759-4760) has been shown to afford, besides stilbene, trace amounts of benzyl p-tolylsulfone; a side condensation (i.e. coupling of phenylcarbene with lithium p-toluenesulfinate) which is precisely the reverse of the decomposition being advocated.