A NEW TIED-BACK APPROACH TOWARD THE SYNTHESIS OF TETRA-TERT-BUTYLETHYLENE

被引：15

作者：

BROOKS, PR

BISHOP, R

CRAIG, DC

SCUDDER, ML

COUNTER, JA

机构：

[1] UNIV NEW S WALES,SCH CHEM,KENSINGTON,NSW 2033,AUSTRALIA

[2] UNIV ADELAIDE,DEPT PHYS & INORGAN CHEM,ADELAIDE,SA 5000,AUSTRALIA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 22期

关键词：

D O I：

10.1021/jo00074a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The extremely hindered selenadiazoline 1,1'',5,5''-tetramethyldispiro[3,7-dithiabicyclo[3.3.1]nonane-9,2'-DELTA3-1',3',4'-selenadiazoline-5',9''-3'',7''-dithiabicyclo[3.3.1]nonane] (6) has been prepared as a precursor to bis(1,5-dimethyl-3,7-dithiabicyclo[3.3.1]non-9-ylidene) (8), a 'tied-back'' analogue of tetra-tert-butylethylene (1). The pyrolysis of 6 yields retrocyclization and decomposition products and no 8, presumably due to strain limitations. The ketone 1,5-dimethyl-3,7-dithiabicyclo[3.3.1]nonan-9-one (4) is unreactive toward McMurry coupling to 8.

引用

页码：5900 / 5906

页数：7

共 33 条

[1] OLEFIN SYNTHESIS BY 2-FOLD EXTRUSION PROCESSES .3. SYNTHESIS AND PROPERTIES OF HINDERED SELENOKETONES (SELONES)
BACK, TG
BARTON, DHR
BRITTENKELLY, MR
GUZIEC, FS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (19): : 2079 - 2089
[2] SYNTHESIS AND PROPERTIES OF MONOMERIC SELENOKETONES
BACK, TG
BARTON, DHR
BRITTENKELLY, MR
GUZIEC, FS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (13) : 539 - 539
[3] OLEFIN SYNTHESIS BY 2-FOLD EXTRUSION PROCESSES .2. SYNTHESIS OF SOME VERY HINDERED OLEFINS
BARTON, DHR
GUZIEC, FS
SHAHAK, I
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (15): : 1794 - 1799
[4] PREPARATION AND CRYSTAL-STRUCTURE OF A TWIN TWIST-BOAT BICYCLO[3.3.1]NONANE MONOHYDRATE
BISHOP, R
CRAIG, DC
SCUDDER, ML
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08): : 1473 - 1477
[5] TETRAKIS(1-METHYLCYCLOPROPYL)ETHYLENE IN 4 STEPS FROM ALPHA-METHYL-GAMMA-BUTYROLACTONE
BOHRER, G
KNORR, R
[J]. TETRAHEDRON LETTERS, 1984, 25 (34) : 3675 - 3678
[6] STRUCTURE OF 1,5-DIMETHYL-3,7-DITHIABICYCLO(3.3.1)NONANE-9-SELONE
BROOKS, PR
COUNTER, JA
BISHOP, R
TIEKINK, ERT
[J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 : 1939 - 1941
[7] STRAIN-ENERGY AND STERICALLY - HINDERED CONFORMATION OF OLEFINS - REPRESENTATIONS OF CROSS-BRIDGED TETRA-TERT-BUTYLETHYLENE DERIVATIVES
BURKERT, U
[J]. TETRAHEDRON, 1981, 37 (02) : 333 - 339
[8] PREPARATION AND REACTIONS OF TETRAKIS(2-FORMYL-2-PROPYL)ETHYLENE, AN ACYCLIC DERIVATIVE OF TETRA-TERT-BUTYLETHYLENE
CULLEN, ER
GUZIEC, FS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (08) : 1212 - 1216
[9] TIED-BACK CARBOCYCLIC INTERMEDIATES IN THE PREPARATION OF VERY STERICALLY STRAINED OLEFINS - DERIVATIVES OF TETRA-TERT-BUTYLETHYLENE
CULLEN, ER
GUZIEC, FS
HOLLANDER, MI
MURPHY, CJ
[J]. TETRAHEDRON LETTERS, 1981, 22 (46) : 4563 - 4566
[10] PLANAR BRIDGING THIOLATE IN (PH3P)2CU(MU-SPH)2CU(PPH3)2
DANCE, IG
GUERNEY, PJ
RAE, AD
SCUDDER, ML
[J]. INORGANIC CHEMISTRY, 1983, 22 (20) : 2883 - 2887

← 1 2 3 4 →