Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes

Matthew D. Hassink; Joseph M. Fox

doi:10.1055/s-0031-1290822

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(18): 2843-2850
DOI: 10.1055/s-0031-1290822

special topic

Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes

Matthew D. Hassink

Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA, eMail: jmfox@udel.edu

,

Joseph M. Fox*

Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA, eMail: jmfox@udel.edu

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Abstract

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Abstract

1,2-Disubstituted 3-hydroxymethylcyclopropene derivatives have been synthesized by reacting the dianions of 1-alkyl-3-hydroxymethylcyclopropenes with a range of electrophiles. Additionally, a complementary procedure is described for one-pot sequential alkylation/rearrangement to provide a convenient synthesis of a chiral methylenecyclopropane directly from a 1-alkyl-3-hydroxymethylcyclopropene.

Key words

cyclopropene - chirality - dianions - strained ring systems - rearrangement

Volltext

Referenzen

References

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