Check out the attached link from tirerack as it displays the width of rim to the size of tire. The size of tire is limited by the width of the rim. The 275's are too wide for a 8.5" rim and the 285's would definetly be of a safety concern. You would be pinching the tire too much around the rim. You can probably go with the 275's but I am not certain.
http://www.tirerack.com/tires/...ition
See the 'Rim Width Range" section also in the link above. Putting a wider tire on a narrower rim actually reduces section width.
For example: a tire in the P205/60R15 size is measured on a 6.0" wide wheel and this size tire has an approved rim width range from 5.5" to 7.5" wide. The tire has a section width of 8.23" (209mm) when mounted on a 6.0" wide wheel. If that tire were mounted on all of the rims within its range, the tire's approximate section width would change as follows:
Diff from Measuring Rim...........Rim Width.....Approximate Tire section width 0.5"narrower...........................5.5"..............8.03" Measuring Rim.........................6.0"..............8.23" 0.5" wider...............................6.5"...............8.43" 1.0" wider...............................7.0"..............8.63" 1.5" wider.............................. 7.5"............ 8.83"
Also keep in mind....load rating. 245/40/18 are only 93 rated while 255/40/18 are 95 rated. See my post about load rating a couple weeks ago for further info what is a risk when going below an OEM load rating.