I've made some progress on my page associating Jmol to chemdoodle's sketcher : 
now every new addition/modification to the sketch is immediately reflected on 
the Jmol view's and vice versa.
http://librairiedemolecules.education.fr/outils/scribmol/
It uses pick and message callback to detect modifications from Jmol, and I also 
inserted  "chemDoodle2jmol" statements in chemdoodleweb-sketcher.js where the 
history manager works.
-Paul

PS : I also made implicit carbons visible to suit my need, removed the buttons 
I didn't need from the sketcher, but I think the webpage could still give a 
good idea of this 2 way communication between Chemdoodle and Jmol
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