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Surprisingly, when the oligomerization reaction is carried out with 2,5-bis(tri- n -butylstannyl)thiophene instead of 7 (entry 1, Table 1), the corresponding MALDI-1 and MALDI-3 are essentially superimposable. This result suggests that (i) n -butyl groups are also easily shifted from the tin atom to the growing oligomer chain and (ii) a benzyl-type cleavage of the transferred n -butyl substituent under MALDI conditions must be prominent. At least in the cases where the n -butyl chain was shifted onto the thienyl end-groups, the benzyl-type cleavage should be promoted either by an efficient mesomeric stabilization of the immediately resulting (2-thienyl)methylium cation or by its rearrangement to a stable thiopyrylium cation - 1607
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