Bridgehead substituents effect on the reactivity of bicyclobutane in its reactions with nucleophiles. A comparison with olefinic systems

Carmela Azran, Shmaryahu Hoz

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

The reactivity of bridgehead substituted bicyclobutanes towards nucleophilic attack was compared with that of the analogous vinylic compounds. Ab initio calculations suggest that the substituents exert nearly the same energetic effects on the ground state of the two systems. The observed difference in the reactivity of the two systems stems, therefore, from the different nature of corresponding transition states.

Original languageEnglish
Pages (from-to)11421-11430
Number of pages10
JournalTetrahedron
Volume51
Issue number42
DOIs
StatePublished - 16 Oct 1995

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