NEW YORK -- Shares of General Motors fell below $1 on Friday for the first time in 76 years as the struggling automaker approached a government-imposed restructuring deadline and a likely filing for Chapter 11 bankruptcy protection, according to The Associated Press.

GM shares lost more than 22 percent to fall as low as 87 cents in morning trading. It was the stock's lowest trade since April 18, 1933, according to the Center for Research in Security Prices at the University of Chicago.

Shares rebounded to 89 cents by late morning.

The symbolic drop comes just days ahead of a government-mandated June 1 deadline to restructure. GM is expected to file for Chapter 11 bankruptcy protection by then, which would leave existing shareholders virtually wiped out.