1,3-DIPOLAR CYCLOADDITIONS TO NITROGEN-SUBSTITUTED ALLENES

被引：49

作者：

BROGGINI, G

BRUCHE, L

ZECCHI, G

PILATI, T

机构：

[1] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,VIA GOLGI 19,I-20133 MILAN,ITALY

[2] CTR STUDIO RELAZ STRUTT & REATT CHIM,CNR,VIA GOLGI 19,I-20133 MILAN,ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 03期

关键词：

D O I：

10.1039/p19900000533

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of nitrogen-substituted allenes (2a-h) was treated with 3,5-dichloro-2,4,6- trimethylbenzonitrile oxide (4) in boiling tetrachloromethane. The reaction occurred predominantly (or exclusively) at the α,β double bond. Regardless of the site of cycloaddition, the carbon of the nitrite oxide bonded selectively to the central carbon of the aliene. 4-Methylene-4,5-dihydroisoxazole monoadducts (5) reacted further to form spiro-diadducts. The stereochemistry of one diadduct was determined by X-ray diffraction analysis.

引用

页码：533 / 539

页数：7

共 29 条

[1] ARLANDINI E, 1983, J CHEM RES-S, P170
[2] ARLANDINI E, 1983, J CHEM RES M, P1575
[3] AVERSA NC, 1968, GAZZ CHIM ITAL, V98, P42
[4] BALLABIO M, 1983, J CHEM RES-S, P140
[5] BALLABIO M, 1983, J CHEM RES M, P1317
[6] REGIOSELECTIVITY OF 1,3-DIPOLAR CYCLO-ADDITIONS OF (PHENYLSULFINYL)-ALKENES AND (PHENYLSULFONYL)ALKENES
BARZAGHI, M
BELTRAME, PL
DALLACROCE, P
DELBUTTERO, P
LICANDRO, E
MAIORANA, S
ZECCHI, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (21) : 3807 - 3810
[7] 1,3-DIPOLAR CYCLOADDITIONS .73. RELATIVE DIPOLAROPHILE ACTIVITIES IN CYCLOADDITIONS OF BENZONITRILE OXIDE
BAST, K
CHRISTL, M
HUISGEN, R
MACK, W
[J]. CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (10): : 3312 - 3344
[8] BATTIONI P, 1978, B SOC CHIM FR II-CH, P415
[9] 1,3-CYCLOADDITIONS OF 3,5-DICHLORO-2,4,6-TRIMETHYLBENZONITRILE OXIDE TO 1,1-DIPHENYLALLENE - REINVESTIGATION
BELTRAME, P
BELTRAME, PL
CATTANIA, MG
ZECCHI, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (11): : 1301 - 1303
[10] 3,3'-DIARYL-5-MORPHOLINO-4,5,4',5'-TETRAHYDRO-4,5'-SPIROBI[ISOXAZOLES]- SYNTHESIS BY CYCLOADDITION REACTIONS AND SUBSTITUENT EFFECT ON THE CYCLOADDITION KINETICS
BELTRAME, P
GELLI, G
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (05) : 1539 - 1543

← 1 2 3 →