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Early 380 engines had a single-row timing chain that wears very rapidly and can break unexpectedly, This results in a valve job, and with age the head bolts can stick in the block, ruining the threads. The necessary repair is also expensive, as it requires special steel inserts and a jig to install them (Jig was $1500 a few years back).
Otherwise they are as good as any other M116/M117 engine -- valves every 250,000 miles or so, the rest of the car will be a pile of rust before the bottome end goes.
Convert to the double-row chain if you need a valve job (it's expensive, but less than the work required to repair a broken chain) if it has not been done.
Peter
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1972 220D ?? miles
1988 300E 200,012
1987 300D Turbo killed 9/25/07, 275,000 miles
1985 Volvo 740 GLE Turobodiesel 218,000
1972 280 SE 4.5 165, 000 - It runs!
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