[RaZ]

Hi, I just have two questions.  The mechanism is in the gif file I attached. My first question is going from compound one to compound two, how would you add the chlorine onto the sulfur? I was thinking of hypochlorous acid (HOCl), but would that work...are there any other ways?  Also, does the overall mechanism make sense?? would it work?  I just want to extend the five member ring to a six membered ring via Markovnikov addition...any help would be appreciated; thanks.