Accession Number : AD0676151

Title :   SCOPE AND MECHANISM OF THE ALKALINE DEGRADATION OF HALOPYRAZOLONES.

Descriptive Note : Final rept.,

Corporate Author : MASSACHUSETTS UNIV AMHERST

Personal Author(s) : Carpino,Louis A.

Report Date : 31 AUG 1968

Pagination or Media Count : 5

Abstract : The work of this project began as a search for synthetic routes to cyclopropenones a class of compounds of considerable theoretical interest which were unknown at the time the work was initiated. On the basis of analogy with earlier studies on non-benzenoid aromatic compounds it was thought that these ketones, although highly strained, would probably be capable of isolation in view of their predicted aromaticity. Although this method was not successful, it was possible to synthesize examples of the sulfonyl analogs which, in fact, represent the first examples of 3-ring heterocycles which are potentially aromatic because of possible d-orbital participation. Other important outcomes of the work involve development of a new synthesis of alpha, beta-unsaturated acids and new syntheses of important antipyrine-like compounds as well as mechanistic clarifications of these reactions. A brief outline of the most important results are presented.

Descriptors :   (*NITROGEN HETEROCYCLIC COMPOUNDS, DECOMPOSITION), KETONES, CYCLOPROPANES, ORGANIC SULFUR COMPOUNDS, MOLECULAR ORBITALS, CARBOXYLIC ACIDS, SYNTHESIS(CHEMISTRY)

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE