Hydrazone-initiated carbene/alkyne cascades to form polycyclic products: ring-fused cyclopropenes as mechanistic intermediates

Phong Q Le; Jeremy A May

doi:10.1021/jacs.5b08157

Hydrazone-initiated carbene/alkyne cascades to form polycyclic products: ring-fused cyclopropenes as mechanistic intermediates

J Am Chem Soc. 2015 Sep 30;137(38):12219-22. doi: 10.1021/jacs.5b08157. Epub 2015 Sep 22.

Authors

Phong Q Le¹, Jeremy A May¹

Affiliation

¹ Department of Chemistry, University of Houston , 3585 Cullen Blvd, Room 112, Houston, Texas 77204-5003, United States.

PMID: 26394217
DOI: 10.1021/jacs.5b08157

Abstract

A hydrazone-based carbene/alkyne cascade produced a variety of bridged and fused polycyclic products. NaOSiMe3 is a superior base for conversion of hydrazones to diazoalkanes. A key mechanistic intermediate, a ring-fused cyclopropene, has been isolated and characterized.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alkynes / chemistry*
Cyclopropanes / chemistry*
Hydrazones / chemistry*
Methane / analogs & derivatives*
Methane / chemistry
Molecular Structure
Polycyclic Compounds / chemical synthesis*
Polycyclic Compounds / chemistry

Substances

Alkynes
Cyclopropanes
Hydrazones
Polycyclic Compounds
carbene
cyclopropene
Methane