SSG 1.4 Arrested Development Page
Leading Question
Selective Deprotection
Sodium naphthalide removes only the tosyl group in structure 116. It is known to be capable of removing tosyls, but it is not the type of compound that would remove the other groups. The TBS and TIPS protective groups are both silyl ethers. They are removed using acids or fluorine containing compounds so sodium naphthalide would not be successful in removing them. The carbamate has multiple bonds it shares in structure 116 that would need to be broken in order to be removed from structure 116. With so many bonds, the carbamate would be difficult to remove with any compound.
Narrator: As it turns out, she had gotten up early and had taken pain medication because of a hangover-related headache. However, she mistook the “drowsy eye” alcohol warning for a “winking-eye” alcohol suggestion.
Lucille: When’s the last time you went on a date?
Michael: I just haven’t met anybody who’s not completely self-absorbed and impossible to have a conversation with.
Lucille: If that’s a veiled criticism about me, I won’t hear it and I won’t respond to it.