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I think the investment has to be ''like kind'' per IRS rules
so no a no tax bond wouldNOT qualify if gain was an active biz vs passive bond
but if he has an other active biz investing the capital in that should qualify
my buddy was cashed out of his family [multi-national] biz
but avoided ALL tax by buying stock in the new merged CORP [like kind biz investment]
I would consult a tax att or IRS qualified advisor to be sure
as the rules change often and details matter
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