Shapiro reaction



The Shapiro reaction or tosylhydrazone decomposition is an base.[1][2][3]

Reaction mechanism

In a prelude to the actual Shapiro reaction a nitrogen leaving a vinyllithium compound.

Scope

Although many secondary reactions exist for this alkene.[5] Other reactions of vinyllithium compounds include alkylation reactions with for instance alkyl halides.[6] In general the least substituted alkene is the preferred reaction product.

 

The carbocation.

See also

References

  1. ^ Shapiro, R.H.; Lipton, M.F.; Kolonko, K.J.; Buswell, R.L.; Capuano, L.A. Tetrahedron Lett., 1975, 1811.
  2. ^ Shapiro, R. H. Org. React., 1976, 23, 405. (Review)
  3. ^ Adlington, R.M.; Barret, A.G.M. Acct. Chem. Res., 1983, 16, 55. (Review)
  4. ^ Organic Syntheses Coll. Vol. 5, p.1055 (1973); Vol. 40, p.93 (1960) (Article)
  5. ^ Shapiro, R. H.; Duncan, J. H. Organic Syntheses Coll. Vol. 6, p.172 (1988); Vol. 51, p.66 (1971). (Article)
  6. ^ Organic Syntheses Coll. Vol. 7, p.77 (1990); Vol. 61, p.141 (1983). (Article)
 
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