THE FIRST EXAMPLE OF A TRANSOID AMIDE (IMIDE) IN AN 8-MEMBERED LACTAM

被引：14

作者：

EVANS, PA

HOLMES, AB

COLLINS, I

RAITHBY, PR

RUSSELL, K

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CTR MOLEC RECOGNIT,CAMBRIDGE CB2 1EW,ENGLAND

[2] ZENECA PHARMACEUT,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 22期

关键词：

D O I：

10.1039/c39950002325

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Claisen rearrangement of the ketene aminal derived by selenoxide elimination of the seleno-aminal 1 in refluxing toluene in the presence of dihydropyran yields the expected unsaturated eight-membered lactam derivative 3, as well as two unexpected products 7a and 7b; the major product 7a (resulting from a selenium. re-addition reaction) was shown by X-ray crystallography to be a highly distorted transoid amide (imide)with the largest p-orbital distortion (tau = 50.6 degrees) recorded for a cyclic amide.

引用

收藏

页码：2325 / 2326

页数：2

相关论文

共 18 条

[1] ASCIDIATRIENOLIDE-A IS A 10-MEMBERED LACTONE [J].

CONGREVE, MS ;

HOLMES, AB ;

HUGHES, AB ;

LOONEY, MG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (13) :5815-5816

[2] NEW SYNTHETIC METHODOLOGY FOR THE SYNTHESIS OF 7-SUBSTITUTED TETRAHYDROAZEPIN-2-ONES [J].

EVANS, PA ;

HOLMES, AB ;

RUSSELL, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23) :3397-3409

[3]

EVANS PA, 1992, TETRAHEDRON LETT, V33, P6857

[4] REGIOSELECTIVE NUCLEOPHILIC-ATTACK ON N-BOC-PYROGLUTAMATE ETHYL-ESTER [J].

EZQUERRA, J ;

DEMENDOZA, J ;

PEDREGAL, C ;

RAMIREZ, C .

TETRAHEDRON LETTERS, 1992, 33 (38) :5589-5590

[5] REMOVAL OF FORMYL, ACETYL, AND BENZOYL GROUPS FROM AMIDES WITH CONVERSION INTO THE CORRESPONDING TERT-BUTYL CARBAMATES [J].

GREHN, L ;

GUNNARSSON, K ;

RAGNARSSON, U .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (19) :1317-1318

[6] CONFORMATIONAL ISOMERISM OF AMIDE GROUP - A REVIEW OF IR AND NMR SPECTROSCOPIC EVIDENCE [J].

HALLAM, HE ;

JONES, CM .

JOURNAL OF MOLECULAR STRUCTURE, 1970, 5 (1-2) :1-&

[7] MITTLERE RINGE .7. DIE EIGENSCHAFTEN ALIPHATISCHER LACTAME UND DIE CIS-TRANS-ISOMERIE DER SAUREAMIDGRUPPE [J].

HUISGEN, R ;

BRADE, H ;

WALZ, H ;

GLOGGER, I .

CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (08) :1437-1447

[8] THE TYPE-2 INTRAMOLECULAR IMINO DIELS-ALDER REACTION - SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF BICYCLO[N.3.1] BRIDGEHEAD OLEFIN BRIDGEHEAD LACTAMS [J].

LEASE, TG ;

SHEA, KJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (06) :2248-2260

[9]

LEASE TG, 1992, ADV THEORETICALLY IN, V2, P79

[10] NEW METHOD FOR CONSTRUCTION OF MACROLIDES - STEREOSELECTIVE SYNTHESIS OF (+/-)-PHORACANTHOLIDE-J - PRELIMINARY COMMUNICATION [J].

PETRZILKA, M .

HELVETICA CHIMICA ACTA, 1978, 61 (08) :3075-3078