TANDEM CARBENE INSERTION SEMIPINACOL REARRANGEMENT OF 1-ALKYNYLCYCLOBUTENOLS - A FACILE SYNTHESIS OF 2-ALKENYL-4-CYCLOPENTENE-1,3-DIONES

ZORA, METİN; HERNDON, JAMES

doi:10.1021/jo00083a002

TANDEM CARBENE INSERTION SEMIPINACOL REARRANGEMENT OF 1-ALKYNYLCYCLOBUTENOLS - A FACILE SYNTHESIS OF 2-ALKENYL-4-CYCLOPENTENE-1,3-DIONES

ZORA M., HERNDON J. W.

JOURNAL OF ORGANIC CHEMISTRY, vol.59, no.4, pp.699-701, 1994 (SCI-Expanded, Scopus)

Publication Type: Article / Letter
Volume: 59 Issue: 4
Publication Date: 1994
Doi Number: 10.1021/jo00083a002
Journal Name: JOURNAL OF ORGANIC CHEMISTRY
Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Page Numbers: pp.699-701
Middle East Technical University Affiliated: Yes

Abstract

Reaction of chromium carbene complexes and 1-alkynylcyclobutenols leads to 2-alkenyl-4-cyclopentene-1,3-diones. Initial allkyne insertion affords a highly electrophilic carbene complex, which then undergoes an alkyl shift-ring expansion, ultimately producing 2-alkenyl-4-cyclopentene-1,3-diones.