+ Resolve Article
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter

+ Translate
+ Subscribe to Site Feed
GeoScience Most Shared ContentMost Shared Content

Regioselective reactions of 1-alkylidene-2-oxyallyl cations with furan: control of [4 + 3] cycloaddition, [3 + 2] cycloaddition, and electrophilic substitution

, : Regioselective reactions of 1-alkylidene-2-oxyallyl cations with furan: control of [4 + 3] cycloaddition, [3 + 2] cycloaddition, and electrophilic substitution. Organic Letters 8(18): 4113-4116

The ring opening of alkylidenecyclopropanone acetal under acidic conditions produces the 1-alkylidene-2-oxyallyl cation as an intermediate, which reacts with furan to give the [3 + 2] and [4 + 3] cycloadducts as well as an electrophilic substitution product. The product distribution is controlled by the oxy substituents of the cation and by the solvent employed.


PMID: 16928087

DOI: 10.1021/ol061655t

Other references

MacGillivray, A.D., 1921: Newspecies of Nematinae (Hymenoptora). Journal of the New York Entomological Society, 291: 27-35

Breitner, J.C., 2000: Vascular depression: new light on an established idea?. Journal of Neurology, Neurosurgery, and Psychiatry 70(1): 3-3

Hurtado, J.L.; Lee, C.; Lodwick, D.; Goede, T.; Williams, J.L.; Bolch, W.E., 2012: Hybrid computational phantoms representing the reference adult male and adult female: construction and applications for retrospective dosimetry. Currently, two classes of computational phantoms have been developed for dosimetry calculation: (1) stylized (or mathematical) and (2) voxel (or tomographic) phantoms describing human anatomy through mathematical surface equations and 3D voxel mat...

Ohnimus, H.; Heinkelein, M.; Jassoy, C., 1997: Apoptotic cell death upon contact of CD4+ T lymphocytes with HIV glycoprotein-expressing cells is mediated by caspases but bypasses CD95 (Fas/Apo-1) and TNF receptor 1. Loss of CD4+ T helper lymphocytes is central to the development of immunodeficiency after infection with HIV. In this study, it was demonstrated that contact of primary uninfected CD4+ T lymphocytes with HIV-infected or HIV envelope glycoprotein-e...

Carena, J.; Pérez Magnelli, F.; Puebla, M.; Smuckler, C., 1991: Rhabdomyolysis associated with an iodinated contrast media. A case of rhabdomyolysis associated with an iodinated contrast medium (sodium diatrizoate) in a patient with chronic renal failure is presented for the purpose of discussing this association. Clinical manifestations were: diffuse myalgias, proxima...

Hardy, J.G.; Cornelison, R.Chase.; Sukhavasi, R.C.; Saballos, R.J.; Vu, P.; Kaplan, D.L.; Schmidt, C.E., 2015: Electroactive Tissue Scaffolds with Aligned Pores as Instructive Platforms for Biomimetic Tissue Engineering. Tissues in the body are hierarchically structured composite materials with tissue-specific chemical and topographical properties. Here we report the preparation of tissue scaffolds with macroscopic pores generated via the dissolution of a sacrific...

Prasad, M.L.; Barbacioru, C.C.; Rawal, Y.B.; Husein, O.; Wen, P., 2007: Hierarchical cluster analysis of myoepithelial/basal cell markers in adenoid cystic carcinoma and polymorphous low-grade adenocarcinoma. Distinguishing adenoid cystic carcinoma from polymorphous low-grade adenocarcinoma of the salivary glands is important for their management. We studied the expression of several myoepithelial and basal/stem cell markers (smooth muscle actin, calpo...

Selmi, C.; Mayo, M.J.; Bach, N.; Gish, R.G.; Wright, H.I.; Ishibashi, H.; Gordon, S.C.; Invernizzi, P.; Seldin, M.F.; Podda, M.; Gershwin, M.E., 2002: Occurrence of primary biliary cirrhosis in monozygotic twins. Hepatology 36(4 Part 2): 387A, October

Battaglia, F.C., 1978: Principal substrates of fetal metabolism: fuel and growth requirements of the ovine fetus. In those fetuses studied, the glucose uptake by the fetus has been a major source of calories, although in all instances it has been insufficient to account for the total fuel requirements of the fetus. The glucose/oxygen quotients in different ma...

Dintzis R.Z.; Middleton M.H.; Dintzis H.M., 1985: Inhibition of anti dinitrophenyl antibody formation by high doses of dinitrophenyl polyacrylamide molecules effects of hapten density and hapten valence. High-dose inhibition of anti-DNP (dinitrophenyl) antibody formation by a series of DNP-polyacrylamide molecules of varying hapten density and hapten valence was measured. It was found that a molecule's inhibitory ability correlated directly w...