Smart playlists are empty

I have a strange problem (aren't they all strange). My iphone 3G works fine, but I find that some of my smart playlists are not synching properly. e.g.
I have a smart playlist of a ripped audiobook which each track is converted to an AAC file.
These are visible and play normally in iTunes.
I have tried to load this on my iphone by selecting the playlist in the Music tab.
When I look at the phone, the playlist does not appear.
If I look at the contents of the phone while it is connected to my Mac, I can see the playlist, but it is empty.
I have tried editing the playlist and unchecking the "live update" box, but nothing changes...
Because I thought it was something wrong with the smart playlist, I tried creating a plain playlist and loading it that way. In this case itunes does not display the playlist at all under the music tab.
Ideas??? TIA

This can happen if iPod is set to not sync unchecked
items in iTunes. The playlist name will transfer but
is all tracks in list are unchecked then they will
not be on iPod.
"sync only selected items" is unchecked and smartplaylists items are all checked.
after ipod sync smartplaylist views on itunes seem to be syncronized but when i eject my ipod they're empty...

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