D. Rardon, R. S. Macomber
Mar 1, 1990
Citations
0
Influential Citations
3
Citations
Journal
Journal of Organic Chemistry
Abstract
The free-radical bromination of 3,5-di-tert-butyl-2-hydroxy-1,2-oxaphosphol-3-ene 2-oxide (1b) with N-bromosuccinimide (NBS) gave the corresponding 5-bromo-3,5-di-tert-butyl-2-hydroxy-1,2-oxaphosphol-3-ene 2-oxide (3) in good yield. Bromide 3 underwent methanolysis to give 3,5-di-tert-butyl-2-hydroxy-5-methoxy-1,2-oxaphosphol-3-ene 2-oxide (7) or hydrolysis to 3,5-di-tert-butyl-2,5-dihydroxy-1,2-oxaphosphol-3-ene 2-oxide (8), both crystalline compounds. Treatment of 8 with diazomethane led to dimethyl (Z)-2,2,6,6-tetramethyl-3-oxohept-4-en-5-ylphosphonate (10), indicating that 8 is in equilibrium with its open phosphonic acid isomer