Readers’ forum: Selling shares between jointly owned companies

My client has approached me with a proposal under which he intends to sell 40% of the shares in a company he owns to another company he owns directly in other words not a group company for cash.

There seems to be no commercial reason for this other than to extract cash at favourable capital gains tax rates. I have warned him about transactions in securities and told him that he is unlikely to obtain a clearance. He has come back to me and said that as applying for a clearance is voluntary could he not just do the transaction anyhow and see whether it is challenged by HMRC? I am very uncomfortable about him doing this but I would prefer to be able to provide him with a definitive reason for this.

Can readers point me in the direction of something specific either from HMRC...