Hydrazulene ring systems via heteroatom-assisted [1,2]-shift of oxonium and sulfonium ylides

Organic Letters
Graham K Murphy, F G West


[reaction: see text] Cyclic mixed acetals with pendant diazoketone side chains undergo rearrangement to ether-bridged cycloheptane ring systems on treatment with Cu(hfacac)(2). Stevens [1,2]-shift of an oxonium ylide furnishes the major product (7), in some cases accompanied by minor amounts of a product (8) resulting from [1,2]-shift of a sulfonium ylide. In the subsequent sulfur-triggered cleavage of the bridging ether, the desired bicyclo[5.3.0]heptene was obtained, along with the product of novel S(N)2' attack on the resulting allylic ketal.


Dec 4, 2003·Journal of the American Chemical Society·Fredrik P MarmsäterF G West
May 7, 2004·Organic Letters·Fredrik P MarmsäterF G West
Sep 1, 1986·Journal of the American Chemical Society·E J Roskamp, C R Johnson

❮ Previous
Next ❯


Jun 15, 2011·Chemical Communications : Chem Comm·Deana M JaberMichael P Doyle
Apr 19, 2016·Chemical Communications : Chem Comm·Zhuang SongQing-Long Xu
Apr 12, 2012·Chemistry : a European Journal·Rafael Ballesteros-GarridoJérôme Lacour
Mar 5, 2008·Chemistry : a European Journal·Benedikt Crone, Stefan F Kirsch
Mar 19, 2019·Chemistry : a European Journal·Jiantao ZhangShifa Zhu
May 26, 2017·Chemical Communications : Chem Comm·Xiaofei XuYuanjiang Pan
Oct 17, 2009·Chemical Reviews·Wenyi Zhao

❮ Previous
Next ❯

Trending Feeds


Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Epigenetics Insights from Twin Studies

Find the latest research on epigenetics and twin studies here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.


Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Regulation of Vocal-Motor Plasticity

Dopaminergic projections to the basal ganglia and nucleus accumbens shape the learning and plasticity of motivated behaviors across species including the regulation of vocal-motor plasticity and performance in songbirds. Discover the latest research on the regulation of vocal-motor plasticity here.

Myocardial Stunning

Myocardial stunning is a mechanical dysfunction that persists after reperfusion of previously ischemic tissue in the absence of irreversible damage including myocardial necrosis. Here is the latest research.