Further Ab initio studies on the reactivity of nitrosoketene

Sihyun Ham, David M. Birney

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

The cycloadditions of nitrosoketene with formaldehyde, acetone and 2-propenal were calculated using ab initio molecular orbital theory (MP2/6-31G*). The reactions proceed by the [3+2] pathway via a concerted, planar and pseudopericyclic transition state with a significantly lower barrier rather than by the alternative [4+2]. The transition state asynchronicity can be used to explain the substituent effects on the cycloaddition of ketones with nitrosoketene.

Original languageEnglish
Pages (from-to)5925-5928
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number34
DOIs
StatePublished - Aug 1997

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