SSG 1.4 Arrested Development Page
References Citations, and Glossary
Citation from our article (cite 64):
Sungchul, J.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 5311-5312.
This article proves that sodium naphthalide will remove the tosyl group from structure 116 and gives rationalization for why sodium naphthalide was specifically used. The article provides a table of data that gives the percent yields of amines produced from different sulfonamide reactions with sodium naphthalide.
Articles that cited this cite:
Douglas, C. J.; Hiebert, S.; Overman, L. E. Org. Lett. 2005, 7, 933-936.
Sha, C. K.; Hong, A. W.; Huang, C. M. Org. Lett. 2001, 3, 2177-2179.
Wei, L.; Bell, A.; Warner, S.; Williams, I. D.; Lippard, S. J. J. Am. Chem. Soc. 1986, 108, 8302-8303.
Cites:
Becker, M. H.; Chua, P.; Downham, R.; Douglas, C. J.; Garg, N. K.; Hiebert, S.; Matsouka, R. T.; Middleton, J. A.; Ng, F. W.; Overman, L. E. J. Am. Chem. Soc. 2007, 129, 11987-12002.
Douglas, C. J.; Hiebert, S.; Overman, L. E. Org. Lett. 2005, 7, 933-936.
Sha, C. K.; Hong, A. W.; Huang, C. M. Org. Lett. 2001, 3, 2177-2179.
Sungchul, J.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 5311-5312.
Wei, L.; Bell, A.; Warner, S.; Williams, I. D.; Lippard, S. J. J. Am. Chem. Soc. 1986, 108, 8302-8303.
Glossary
sodium naphthalide: This is a reagent used in this experiment with the structure shown below. It is very important because it causes a deprotection of only the tosyl group on molecule 116 to form molecule 117.
Structure:
Na+
azeotropic distillation: This is a special type of distillation for mixtures of two or more pure compounds in such a ratio that its composition cannot be changed by simple distillation. Different separation agents can be used, but in the case of this experiment benzene was used to break the azeotrope by changing the molecular interactions of the azeotrope.
Michael: Look, I don’t want your forgiveness, Dad. I want the guy with the one arm and the fake blood. J. Walter Weatherman. How do I get a hold of him? George Sr.: Well, he’s, uh, dead. You killed him when you left the door open with the air conditioner on. |
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