REACTIONS OF ETHYL ACETYL-2-AZABICYCLO[2.2.1]HEPT-5-ENE-3-CARBOXYLATEAND 4-ACETYLAMINO-2-OXABICYCLO[3.3.0]OCT-7-EN-3-ONE WITH SOME ELECTROPHILES

Authors
HURSTHOUSE MB MALIK KMA HIBBS DE ROBERTS SM SEAGO AJH SIK V STORER R
Citation
Mb. Hursthouse et al., REACTIONS OF ETHYL ACETYL-2-AZABICYCLO[2.2.1]HEPT-5-ENE-3-CARBOXYLATEAND 4-ACETYLAMINO-2-OXABICYCLO[3.3.0]OCT-7-EN-3-ONE WITH SOME ELECTROPHILES, Journal of the Chemical Society. Perkin transactions. I, (19), 1995, pp. 2419-2425
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
19
Year of publication
1995
Pages
2419 - 2425
Database
ISI
SICI code
0300-922X(1995):19<2419:ROEA>2.0.ZU;2-0
Abstract
The amide 3 reacted with various electrophilic reagents to give the ad dition products 5-9; reaction of 3 with m-chloroperoxybenzoic acid (MC PBA) gave the epoxide 10; similarly, the lactone 4 (an isomer of 3) re acted extremely selectively with a variety of electrophiles to give a range of polyfunctionalised bicyclic systems 12-15: reaction with MCPB A gave the epoxide 16 as the major product.