Tetrahedron

Unexpected regiospecific reactivity of a substituted phthalic anhydride

MJ Petersson, C Marchal, WA Loughlin, ID Jenkins…

Index: Petersson, Maria J.; Marchal, Camille; Loughlin, Wendy A.; Jenkins, Ian D.; Healy, Peter C.; Almesaker, Ann Tetrahedron, 2007 , vol. 63, # 6 p. 1395 - 1401

Full Text: HTML

Citation Number: 17

Abstract

Regioselective nucleophilic addition at C1 of anhydride 7 by a range of nucleophiles occurs to produce amide, ester and thioester derivatives 8–15 (60–99%). The increased electrophilic reactivity of the C1 carbonyl group of anhydride 7 is supported by a competition experiment with phthalic anhydride. Unexpected formation of lactams 18 and 19 from amides 12 and 13 was shown to proceed via the lactamols 16 and 17 and could be ...

Related Articles:

Diels–Alder Reactions of Masked o??Benzoquinones with 1??Vinylcyclohexenes: A Short and Efficient Entry to Highly Functionalized Decahydrophenanthrene Skeleton

[Niu, Guang-Hao; Hou, Chieh-Shen; Chuang, Gary Jing; Wu, Chi-Phi; Liao, Chun-Chen European Journal of Organic Chemistry, 2014 , vol. 2014, # 18 p. 3794 - 3801]

Highly stereoselective hydroxy-directed Diels-Alder reaction

[Barriault, Louis; Thomas, Jermaine D. O.; Clement, Roxanne Journal of Organic Chemistry, 2003 , vol. 68, # 6 p. 2317 - 2323]

1, 3-Oxidative Rearrangements of Dienols

[Majetich, George; Condon, Stephen; Hull, Kenneth; Ahmad, Saeed Tetrahedron Letters, 1989 , vol. 30, # 9 p. 1033 - 1036]

The Rearrangement of 2, 3-Epoxysulfonates and Its Application to Natural Products Syntheses: Formal Synthesis of (-)-Aphanorphine and Total Syntheses of (-)-α- …

[Crisan; Normant Bulletin de la Societe Chimique de France, 1957 , p. 1451,1453]

Two methods for the preparation of 2-cyclohexenones from resin-bound 1, 3-cyclohexanedione

[Fraley, Mark E.; Rubino, Robert S. Tetrahedron Letters, 1997 , vol. 38, # 19 p. 3365 - 3368]

More Articles...