COMPETITIVE REARRANGEMENTS .4. NEOPENTYLIC VERSUS SKELETAL REARRANGEMENT IN THE REACTION OF 7-T-BUTYL-DIBENZOBICYCLO[2.2.2] OCTATRIENE AND OF ITS 8-CARBOMETHOXY DERIVATIVE WITH CHLORINE

Authors
BRAVERMAN S GOTTLIEB H IONICA I BADEA F DINULESCU IG
Citation
S. Braverman et al., COMPETITIVE REARRANGEMENTS .4. NEOPENTYLIC VERSUS SKELETAL REARRANGEMENT IN THE REACTION OF 7-T-BUTYL-DIBENZOBICYCLO[2.2.2] OCTATRIENE AND OF ITS 8-CARBOMETHOXY DERIVATIVE WITH CHLORINE, Revue Roumaine de Chimie, 39(8), 1994, pp. 985-988
Citations number
3
Categorie Soggetti
Chemistry
Journal title
Revue Roumaine de Chimie → ACNP
ISSN journal
00353930
Volume
39
Issue
8
Year of publication
1994
Pages
985 - 988
Database
ISI
SICI code
0035-3930(1994)39:8<985:CR.NVS>2.0.ZU;2-1
Abstract
The reaction of parent compound 1 with chlorine occurs with skeletal r earrangement, yielding a mixture of 6 and 7. In the reaction of 2 with chlorine,, two types of rearrangement are competitive: the neopentyli c, affording 8 and 9, and the skeletal rearrangement, yielding 10; at longer time the chloro-lactone 9 becomes the single reaction product, evidencing a retro-re arrangement [3.2.1] --> [2.2.2] of 10. A mechani sm of these reactions is proposed.