Novel Nano- and Micro-Processing by Photoactivation of Methylene Iodide Precursor

2019 ◽  
Vol 25 (24) ◽  
pp. 65-71
Author(s):  
Abdul Rashid ◽  
Lars Landström ◽  
Klaus Piglmayer
Keyword(s):  
1984 ◽  
Vol 15 (25) ◽  
Author(s):  
J. R. FEHLNER ◽  
P. J. BOROWSKI ◽  
P. L. PETTINATO ◽  
A. J. FREYER

2005 ◽  
Vol 75 (2) ◽  
pp. 240-243
Author(s):  
R. D. Gigauri ◽  
L. G. Arabuli ◽  
Z. N. Machaidze ◽  
M. Sh. Rusiya

2009 ◽  
Vol 82 (7) ◽  
pp. 910-913 ◽  
Author(s):  
Yosuke Sakamoto ◽  
Akihiro Yabushita ◽  
Masahiro Kawasaki ◽  
Tomoki Nakayama ◽  
Yutaka Matsumi

1964 ◽  
Vol 86 (7) ◽  
pp. 1347-1356 ◽  
Author(s):  
Howard E. Simmons ◽  
Elwood P. Blanchard ◽  
Ronald D. Smith

1972 ◽  
Vol 50 (18) ◽  
pp. 2919-2927 ◽  
Author(s):  
Bert Fraser-Reid ◽  
Bruno Radatus

The homoallyl iodide 4,6-O-benzylidene-1,2,3-trideoxy-D-ribo-hex-1-enopyranose, 4, is the second major product from Simmons–Smith reaction of methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopy-ranoside, 6α. The major product is the cyclopropyl glycoside 7α, which when treated separately with the Simmons–Smith reagents furnishes an 85% yield of 4. The mechanism of this transformation is investigated. It is not simply a Lewis-catalyzed iodinolysis since zinc iodide in a variety of solvents does not convert 7α to 4. Methylene iodide is essential, as is the organo-zincate complex, operative in Simmons–Smith reactions.The 3-epimer of the homoallyl iodide 4, i.e. 4,6-O-benzylidene-1,2,3-trideoxy-D-arbino-hex-1-enopyranose, 5, is produced in only 0.9% yield in the methylenation of the anomeric olefinic glycoside, 6β. The low yield is attributable to the extensive anomerization experienced by 6β itself, and by the primary reaction products. This leads to a plethora of compounds including both epimeric homoallyl iodides 4 and 5.In order to get it all together, the homoallyl iodide 4 is transformed into its epimer 5 by an unambiguous synthetic sequence. Some of the intermediates in this sequence are polyfunctional molecules of considerable synthetic potential.The possibility of an alternative route to compound 4 directly from the olefinic glycoside 6α is discussed. Coordination of the methoxyl oxygen of 6α to the organo-zincate complex could achieve an ideal SNi transition state in which [Formula: see text] is delivered at C-3 with synchronous departure of the methoxyl group. This mechanism, called the "reverse" allylic rearrangement for reasons outlined in the text, is discussed.


2001 ◽  
Vol 08 (03n04) ◽  
pp. 303-312 ◽  
Author(s):  
G. WU ◽  
D. STACCHIOLA ◽  
M. COLLINS ◽  
W. T. TYSOE

The adsorption of methylene iodide and methyl iodide is studied on Ag(111) using reflection-absorption infrared spectroscopy. Molecular methylene iodide adsorbs in a random orientation at 80 K and converts into a species with the H–C–H plane adsorbed perpendicular to the surface on heating to 155 K, and also dissociates into iodomethyl species. These undergo further decomposition eventually to form ethylene, although no methylene species are detected on the surface. Methyl iodide forms both multilayers and a metastable state on Ag(111) at 180 K, where the C–I axis of the metastable state is oriented nearly parallel to the surface. Infrared data suggest that the metastable state both desorbs almost simultaneously with the multilayer and converts to adsorbed methyl iodide with the C–I axis oriented nearly perpendicular to the surface. The latter species decomposes into adsorbed methyl fragments and adsorbed iodine where the frequency of the methyl bending mode for CH3(ads) and for CH3I(ads) are identical at 1230 cm -1.


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