use strict;
my $str = '<!-- The following should match. Not the dashes in the comment tag, obviously ;P -->
<h2 class="chapter_title">Chapter 01 -- The Beginning</h2>
<h2 class="chapter_title">Chapter 02 - The Reckoning</h2>
<h2 class="chapter_title">Chapter 03 - - The Aftermath</h2>
<h2 class="chapter_title">Chapter 04--The Conclusion</h2>
<p>I was having the usual - cheeseburger and a cold beer.</p>
<!-- The following should not match -->
<p>I was wearing a t-shirt.</p>
<p>It was a drunken mix-up</p>
<p>---</p>
<p>-----</p>
<p>- - -</p>
<p> - - </p>
<p> - - - </p>
';
my $regex = qr/(?<=\w)(?<!\w-\w)(?: ?-+ ?)+(?=\w)(?!\w-\w)/mp;
my $subst = '—';
my $result = $str =~ s/$regex/$subst/rg;
print "The result of the substitution is' $result\n";
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for Perl, please visit: http://perldoc.perl.org/perlre.html