Stereocontrolled double ring expansion of fused allylidenecyclopropanes. A novel route to hydroazulenes and other fused bicyclic systems

1993 ◽  
Vol 115 (23) ◽  
pp. 10754-10773 ◽  
Author(s):  
Craig A. Shook ◽  
Matthew L. Romberger ◽  
Sang Hun Jung ◽  
Manchao Xiao ◽  
James P. Sherbine ◽  
...  
Keyword(s):  
Ring Expansion ◽  
Double Ring

Double Ring Expansion from an Aromatic [18]Porphyrin(1.1.1.1) to an Antiaromatic [20]Porphyrin(2.1.2.1)

2016 ◽  
Vol 55 (28) ◽  
pp. 8095-8099 ◽  
Author(s):  
Masataka Umetani ◽  
Takayuki Tanaka ◽  
Taeyeon Kim ◽  
Dongho Kim ◽  
Atsuhiro Osuka
Keyword(s):  
Ring Expansion ◽  
Double Ring

Trihydroborates and Dihydroboranes Bearing a Pentacoordinated Phosphorus Atom: Double Ring Expansion To Balance the Coordination States

2017 ◽  
Vol 56 (21) ◽  
pp. 5882-5885 ◽  
Author(s):  
Naokazu Kano ◽  
Nathan J. O'Brien ◽  
Ryohei Uematsu ◽  
Romain Ramozzi ◽  
Keiji Morokuma
Keyword(s):  
Phosphorus Atom ◽  
Ring Expansion ◽  
Double Ring ◽  
Pentacoordinated Phosphorus

Cascade Radical Cyclization-Fragmentation-Transannular-Ring Expansion Reactions Involving Oximes. A New Approach to Synthesis of Angular Triquinanes

1995 ◽  
Vol 48 (2) ◽  
pp. 381 ◽  
Author(s):  
GJ Hollingworth ◽  
G Pattenden ◽  
DJ Schulz
Keyword(s):  
Main Product ◽  
Ring Expansion ◽  
Radical Cyclization ◽  
One Pot ◽  
New Approach ◽  
Vinyl Bromide ◽  
Radical Intermediates ◽  
Double Ring ◽  
Radical Fragmentation ◽  
Aminyl Radical

Treatment of the acetylene-substituted cyclobutanone oxime ether (13) with (Me3Si)3SiH leads, in one pot, to the 5,6-bicyclic enone oxime (14) in 70% yield. It is suggested that the formation of (14) from (13) proceeds by way of a novel double ring expansion-transannulation process involving aminyl radical intermediates (see Scheme 3, below). By contrast, treatment of the cyclobutanone (3a) with Bu3SnH instead leads only to the product (11) of hydrostannylation of the acetylene unit in (3a). Neither (3a) nor (13) produced any of the expected bicyclo[3.3.0]octane products, viz. (5a) and (15), following treatment with silanes or stannanes. When a solution of the vinyl bromide-substituted cyclobutanone oxime (42) was irradiated with a sunlamp in the presence of (Me3Si)3SiH, the main product isolated was the triquinane (45) (38%) resulting from a cascade radical 6-exo-trig cyclization, aminyl radical fragmentation, 5-exo-trig radical transannulation, 5-exo-trig cyclization sequence.

The Cyclopropylalkylidenecyclopropane Thermal Double Ring Expansion. A Novel Route to the Bicyclo[5.3.1]undecane Skeleton of the AB Ring System of Taxanes1

1998 ◽  
Vol 120 (3) ◽  
pp. 605-606 ◽  
Author(s):  
Hong Liu ◽  
Craig A. Shook ◽  
James A. Jamison ◽  
Mohan Thiruvazhi ◽  
Theodore Cohen
Keyword(s):  
Ring Expansion ◽  
Ring System ◽  
Double Ring ◽  
Ab Ring

scholarly journals Isolation of a Bis-Iodurated Tetra-THF as a Trace Product from the Oxidation of Squalene with RuO4 and Its Double Ring Expansion to a Novel bis-THF-bis-THP Compound

Molecules ◽  
2011 ◽  
Vol 16 (7) ◽  
pp. 5362-5373 ◽  
Author(s):  
Vincenzo Piccialli ◽  
Sabrina Zaccaria ◽  
Roberto Centore ◽  
Angela Tuzi ◽  
Nicola Borbone ◽  
...  
Keyword(s):  
Ring Expansion ◽  
Double Ring

Trihydroborates and Dihydroboranes Bearing a Pentacoordinated Phosphorus Atom: Double Ring Expansion To Balance the Coordination States

2017 ◽  
Vol 129 (21) ◽  
pp. 5976-5979 ◽  
Author(s):  
Naokazu Kano ◽  
Nathan J. O'Brien ◽  
Ryohei Uematsu ◽  
Romain Ramozzi ◽  
Keiji Morokuma
Keyword(s):  
Phosphorus Atom ◽  
Ring Expansion ◽  
Double Ring ◽  
Pentacoordinated Phosphorus

Double Ring Expansion from an Aromatic [18]Porphyrin(1.1.1.1) to an Antiaromatic [20]Porphyrin(2.1.2.1)

2016 ◽  
Vol 128 (28) ◽  
pp. 8227-8231 ◽  
Author(s):  
Masataka Umetani ◽  
Takayuki Tanaka ◽  
Taeyeon Kim ◽  
Dongho Kim ◽  
Atsuhiro Osuka
Keyword(s):  
Ring Expansion ◽  
Double Ring
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