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We recently collapsed an existing site in order to relaunch it as a much smaller, much higher quality site. In doing so, we're facing some indexation issues whereas a large number of our old URLs (301'd where appropriate) still show up for a site:domain search.

Some relevant notes:

• We transitioned the site from SiteCore to Wordpress to allow for greater flexibility
• The Wordpress CMS went live on 11/22 (same legacy content, but in the new CMS)
• The new content (and all required 301s) went live on 12/2
• The site's total number of URLS is currently at 173 (confirmed by ScreamingFrog)
• As of posting this question, a site:domain search shows 6,110 results

While it's a very large manual effort, is there any reason to believe that submitting removal requests through Google Webmaster Tools would be helpful?

We simply want all indexation of old pages and content to disappear - and for Google to treat the site as a new site on the same old domain.

A site we've been working on and doing well with (relatively new) got hit pretty hard on November 4th and 5th. Since then, traffic is down considerably and we're trying to diagnose what specific triggers may have caused such a change.