Expenditure on ensuring that a company’s issued shares do
not change hands is capital, but in those circumstances the
expenditure will in any event clearly fall foul of ICTA88/S74
(1)(a) - see
BIM38275. Where, exceptionally, a
deduction is claimed for losses on the sale of shares purchased as
part of a (possibly illegal) price support operation, the capital
argument may well have independent significance.
There is detailed guidance on the capital/revenue divide at
BIM35000 onwards.
Finally, you should not overlook the disallowance of
expenditure on gifts and entertaining under ICTA88/S577, incurred
for example to maintain the loyalty of existing shareholders - see
BIM45000 onwards.