EASY PREPARATION OF A CYCLOBUTANONE KETAL VIA A RADICAL CYCLIZATION - THE GEM-DIALKOXY EFFECT

被引：62

作者：

JUNG, ME

TRIFUNOVICH, ID

LENSEN, N

机构：

[1] Deparment of Chemistry and Biochemistry, University of California, Los Angeles

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(00)61759-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the facile synthesis of cyclobutanones, the key step of which is a radical cyclization to generate the four-membered ring, is reported. In addition, a comparison of the gem-dialkyl and gem-dialkoxy effects in radical cyclizations to give cyclobutane systems shows that in this system the gem-dialkoxy effect is the larger.

引用

页码：6719 / 6722

页数：4

共 17 条

[11] GEM-DIALKYL EFFECT IN THE INTRAMOLECULAR DIELS-ALDER REACTION OF 2-FURFURYL METHYL FUMARATES - THE REACTIVE ROTAMER EFFECT, ENTHALPIC BASIS FOR ACCELERATION, AND EVIDENCE FOR A POLAR TRANSITION-STATE
JUNG, ME
GERVAY, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) : 224 - 232
[12] ACCELERATION OF THE 4-EXO RADICAL CYCLIZATION TO A SYNTHETICALLY USEFUL RATE - CYCLIZATION OF THE 2,2-DIMETHYL-5-CYANO-4-PENTENYL RADICAL
PARK, SU
VARICK, TR
NEWCOMB, M
[J]. TETRAHEDRON LETTERS, 1990, 31 (21) : 2975 - 2978
[13] A NEW SYNTHETIC ROUTE TO (+/-)-THIENAMYCIN VIA 4-EXO TRIGONAL CYCLIZATION OF CARBAMOYL COBALT INTERMEDIATES
PATTENDEN, G
REYNOLDS, SJ
[J]. TETRAHEDRON LETTERS, 1991, 32 (02) : 259 - 262
[14] REACTIONS OF 3,3,4,4-TETRAFLUOROHEXA-1,5-DIENE .2. CYCLISATION TO A 4-MEMBERED RING IN THERMAL ADDITION OF PENTAFLUOROIODOETHANE
PICCARDI, P
MODENA, M
CAVALLI, L
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (23): : 3959 - &
[15] PICCARDI P, 1973, J CHEM SOC P1, P982
[16] CHIRAL SYNTHONS FROM CARVONE .6. A REGIOSPECIFIC AND STEREOSPECIFIC RADICAL ANNULATION ROUTE TO CHIRAL TRICYCLO[4.3.1.0(3,7)]DECANE (ISOTWISTANE) SYSTEM SYNTHESIS OF (+)-10-ALPHA-NAPHTHYL-5-EPI-PUPUKEAN-9-ONE
SRIKRISHNA, A
HEMAMALINI, P
SHARMA, GVR
[J]. TETRAHEDRON LETTERS, 1991, 32 (45) : 6609 - 6610
[17] INTRAMOLECULAR DIELS-ALDER REACTIONS WITH FURAN - THE GEM-DIALKYL EFFECT REVISITED
STERNBACH, DD
ROSSANA, DM
ONAN, KD
[J]. TETRAHEDRON LETTERS, 1985, 26 (05) : 591 - 594

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