GM shares lost more than 22 percent to fall as low as 87 cents in morning trading on Friday. It was the stock's lowest trade since April 18, 1933.

The symbolic decline comes just days away from a government-imposed restructuring deadline of June 1. The company is expected to file for Chapter 11 bankruptcy protection by then, leaving shareholders virtually wiped out.

On Thursday, the automaker offered a new debt-for-equity proposal to its bondholders. The deal would give the government a 72.5 percent stake in the company but made no mention of existing shareholders.

GM has until Monday to complete a government-ordered restructuring that includes debt reduction, labor cost cuts and plant closures. But a Chapter 11 reorganization is likely after the company said its offer to exchange $27 billion in unsecured debt for 10 percent of the company's stock had failed. GM has received $19.4 billion in federal loans.

The move came as crosstown rival Chrysler LLC headed to court Wednesday to ask bankruptcy judge for permission to sell the bulk of its assets to a group headed by Italy's Fiat Group SpA in hopes of saving itself from liquidation. Attorneys for Chrysler maintain that the Fiat deal is the company's only hope to avoid being sold piece by piece, but car dealers, debtholders, former employees and others are protesting.

Chrysler filed for bankruptcy protection April 30, after the government ended talks with a group of holdout debtholders. Both automakers were pulled down by overwhelming debt, high pension, health care and other labor costs relative to competitors, a global auto sales slump and a dismal U.S. housing market that pulled down demand for pickup trucks, their top-selling vehicles.

News of the failed GM bond exchange offer sent its shares down 12 cents, or 8.3 percent, to $1.32 in morning trading.

John Pottow, a professor at the University of Michigan who specializes in bankruptcy, said GM evading Chapter 11 now is almost impossible.

The justices without comment Tuesday left in place a ruling by the Tennessee Court upholding the damages against Chrysler LLC.

The lawsuit claimed 8-month-old Joshua Flax was riding in the back seat of a 1998 Dodge Caravan in Nashville, Tenn., in 2001 when the vehicle was rear-ended, causing the front passenger seat to collapse and the passenger to strike him, fracturing his skull.

A jury initially awarded Flax's parents $98 million in punitive damages in 2004, but the damages were later reduced. The family was also awarded $5 million in compensatory damages, which were upheld by an appeals court.

The third-largest U.S. automaker filed for bankruptcy protection in April.

The privately held company also reached a deal that will allow a Crown Acquisitions affiliate to buy 17 of its 25 stores, including its flagship locations in Boston and New York. The agreement is subject to a bankruptcy court auction, which is expected in about five weeks.

The auction will allow other companies to submit bids for the 17 stores, as well as for the rest of the Filene's Basement locations and the chain's other assets.

New York-based Crown, a real estate and asset management company, plans to continue running the 17 stores under the Filene's Basement name.

Buxbaum Group, a California-based liquidator, acquired Filene's last month through an affiliate company, FB II Acquisition Corp. The sale came after the previous owner, Retail Ventures Inc., said the chain was experiencing "significant liquidity problems."

Filene's Basement, known for its "Running of the Brides" wedding gown sale, was founded more than a century ago in Boston.

"We worked very hard to keep this company out of bankruptcy," one official said on a conference call with reporters. However, not all of Chrysler's secured creditors were on board with the agreement. "With reluctance, we've made the decision to go through with this surgical bankruptcy process."

Under the terms of the arrangement, Chrysler will be placed in a "quick rinse" bankruptcy, which officials expect to last about 30 to 60 days. The government will provide $3 billion to $3.5 billion so-called "debtor in possession" financing to keep the company running, and another $4.5 billion in exit financing. In addition, the Canadian government will provide $1 for every $3 of U.S. taxpayer money on the line.

The government is also replacing Chrysler's board, but it is not yet clear who the replacements will be. Officials said Chrysler Financial, the company's captive financing arm, didn't have the resources to support a restructuring. Instead, GMAC will be the company's new financing source, with support from the U.S. government. Italian automaker Fiat will engage in a partnership agreement with the company.

Fiat's stake would initially be 20%, but it could increase, in 5% increments, as it meets three government thresholds: helping Chrysler establish a distribution network outside of North America, building a fuel-efficient engine in a Chrysler U.S. Factory, and building a small car in a U.S. Factory. Once taxpayers are repaid, Fiat could boost its stake above 50%.

Seattle-based WaMu, which filed for Chapter 11 reorganization along with its Washington Mutual Investment Corp. affiliate in September, contends in the complaint that the funds are part of its bankruptcy estate.

The complaint was filed in U.S. Bankruptcy Court in Delaware on Monday, one month after New York-based JPMorgan filed its own adversary action asserting that the funds were included in its $1.9 billion purchase of substantially all of WaMu's banking assets from the Federal Deposit Insurance Corporation.

A Manhattan judge cleared the way for the newly filed Chapter 7 petition last week by granting a request from the same investors to lift a temporary order barring bankruptcy for Madoff. They had argued that a bankruptcy case was needed to protect their rights amid an ongoing scramble to seize his assets.

Madoff, 70, pleaded guilty last month to federal charges his secretive investment advisory service actually was a multibillion Ponzi scheme in which he paid longtime clients with money from new ones. He is jailed, awaiting a June sentencing for charges that carry a sentence of up to 150 years in prison.

Federal authorities already have begun forcing Madoff to forfeit property they allege was paid for by his fraud. In addition, a court-appointed trustee is liquidating assets from his securities firm to help play claims from thousands of burned investors.

The investors who sought bankruptcy believe it was the best way to make sure "all the property available would go to the victims," their lawyer, Jonathan Landers, said Monday.

They include a general partnership in Florida that claims it lost $30.2 million and another Madoff client who says he lost about $29 million in personal and charitable trust accounts. The claims are based on amounts listed in the last statements they received from Madoff — documents investigators say were fictitious.