IMPROVED SYNTHESIS OF 6,6,7,7-TETRAMETHYL-1-AZABICYCLO[2.2.2]OCTAN-2-ONE AND ITS STABILITY TOWARD BASE-INDUCED METHANOLYSIS

The published method for synthesis of the bridgehead lactam ,6,7,7-tet ramethyl-1-azabicy-clo[2.2.2]octan-2-one yields polymers almost exclus ively. Use of dilution techniques provides a 27% yield of this highly strained molecule. Base-induced methanolysis of this tetramethyl compo und occurs exceedingly slowly compared to some other less crowded homo logues. A buttressing effect is postulated to account for part of this effect.