REACTION OF ETHYL ALPHA-CHLORO-ALPHA-PHENYLSELENOACETATE WITH ALKENES- SYNTHESIS OF ALPHA-PHENYLSELENO-GAMMA-BUTYROLACTONES

Authors
SILVEIRA CC ARAUJO MA LENARDAO EJ BRAGA AL DABDOUB MJ
Citation
Cc. Silveira et al., REACTION OF ETHYL ALPHA-CHLORO-ALPHA-PHENYLSELENOACETATE WITH ALKENES- SYNTHESIS OF ALPHA-PHENYLSELENO-GAMMA-BUTYROLACTONES, Synthesis, (10), 1995, pp. 1305
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
10
Year of publication
1995
Database
ISI
SICI code
0039-7881(1995):10<1305:ROEAWA>2.0.ZU;2-6
Abstract
Ethyl alpha-chloro-alpha-phenylselenoacetate (1) reacts with alk-1-ene s in the presence of TiCl4 to give the corresponding alpha-phenylselen o gamma,delta-unsaturated esters. Reaction of 1 with di- and trisubsti tuted alkenes and SnCl4 as a Lewis acid affords gamma-butyrolactones d irectly and a minor amount of the gamma,delta-unsaturated esters. Thes e esters were converted into gamma-butyrolactones on hydrolysis and re action with electrophiles.