Preparation of methyl carbamates from primary alkyl-and arylcarboxamides using hypervalent iodine

…, RK Vaid, O Prakash, SM Tuladhar

Index: Moriarty, Robert M.; Chany, Calvin J.; Vaid, Rahde K.; Prakash, Om; Tuladhar, Sudersan M. Journal of Organic Chemistry, 1993 , vol. 58, # 9 p. 2478 - 2482

Full Text: HTML

Citation Number: 95

Abstract

A series of 14 primary alkyl-and arylcarboxarnides were treated with PhI (0Ac) z in KOH- CH30H at 5-10 OC to give the corresponding methyl carbamates in good to excellent yields. These conditions avoid the use of elemental bromine or heavy metal reagents (Pb (OAc) r, AgOAc, Hg (OAc) z), while taking advantage of the commercial availability of PhI (0Ac) e. The methyl carbamates are easily purified via column chromatography on silica gel. The ...

Related Articles:

Indium-catalyzed reaction for the synthesis of carbamates and carbonates: selective protection of amino groups

[Kim, Joong-Gon; Jang, Doo Ok Tetrahedron Letters, 2009 , vol. 50, # 22 p. 2688 - 2692]

Palladium??Catalyzed Carbonylation of Amines: Switchable Approaches to Carbamates and N, N′??Disubstituted Ureas

[Guan, Zheng-Hui; Lei, Hao; Chen, Ming; Ren, Zhi-Hui; Bai, Yinjuan; Wang, Yao-Yu Advanced Synthesis and Catalysis, 2012 , vol. 354, # 2-3 p. 489 - 496]

Chloroformate Free, Scalable Approach for the Synthesis of Organic Carbamates and Their Alkylation

[Shewalkar, Mukesh P.; Rao, Ramakrishna R.; Reddy, Veerbhadra; Darandale, Sunil N.; Shinde, Devanand B. Letters in Organic Chemistry, 2013 , vol. 10, # 1 p. 60 - 64]

Photolysis and Thermolysis of Pyridyl Carbonyl Azide Monolayers on Single??Crystal Platinum

[Adkinson, Dana K.; Magri, David C.; Pitters, Jason L.; Griffiths, Keith; Norton, Peter R.; Workentin, Mark S. Photochemistry and Photobiology, 2013 , vol. 89, # 5 p. 1020 - 1028]

Unexpected reaction of oximinoacetoacetate with amines: A novel synthesis of carbamates

[Elghamry, Ibrahim Synthetic Communications, 2009 , vol. 39, # 17 p. 3010 - 3015]

More Articles...