A federal police raid on the eastern suburbs office of property development firm Rommark turned violent on Wednesday when company director Michael Teplitsky crash tackled a photographer and was handcuffed in front of horrified shoppers.

Australian Federal Police officers raided the company's Double Bay office on Wednesday morning, as officers conducted raids across Sydney as part of a wider investigation into an alleged $165 million tax fraud syndicate.

Officers sort through documents in the Double Bay office of property development company Rommark. Credit:Fairfax Media

Nine people were arrested on Wednesday as part of that investigation, including Adam Cranston, the son of Australian Taxation Office deputy commissioner Michael Cranston. He was arrested in Bondi and is due to face Central Local Court on Thursday.

There is no suggestion Michael Cranston had any involvement in or knowledge of the alleged syndicate.