DOI: 10.1021/ja991094j. A New Class of Iodonium Ylides Engineered as Soluble Primary Oxo and Nitrene Sources

A New Class of Iodonium Ylides Engineered as Soluble Primary Oxo and Nitrene Sources

10.1021/ja991094j

Crossref journal-article

American Chemical Society (ACS)

Journal of the American Chemical Society (316)

Bibliography

Macikenas, D., Skrzypczak-Jankun, E., & Protasiewicz, J. D. (1999). A New Class of Iodonium Ylides Engineered as Soluble Primary Oxo and Nitrene Sources. Journal of the American Chemical Society, 121(30), 7164â7165.

Authors 3

Dainius Macikenas (first)
Ewa Skrzypczak-Jankun (additional)
John D. Protasiewicz (additional)

References 24 Referenced 175

{'key': 'ja991094jb00001/ja991094jb00001_1', 'volume-title': 'Science', 'author': 'Some', 'year': '1993'} / Science by Some (1993)
{'key': 'ja991094jb00002/ja991094jb00002_1', 'first-page': '362', 'volume': '361', 'author': 'Yamada Y.', 'year': '1975', 'journal-title': 'Chem. Lett.'} / Chem. Lett. by Yamada Y. (1975)
{'key': 'ja991094jb00003/ja991094jb00003_1', 'first-page': '1715', 'volume': '8', 'author': 'Osborn H. M. I.', 'year': '1997', 'journal-title': 'Tetrahedron Asym.'} / Tetrahedron Asym. by Osborn H. M. I. (1997)
10.1021/cr970343o / Chem. Rev. by Johannsen M. (1998)
10.1021/cr950016l / Chem. Rev. by Lautens M. (1996)
10.1002/anie.199405991 / Angew. Chem., Int. Ed. Engl. by Tanner D. (1994)
{'key': 'ja991094jb00004/ja991094jb00004_1', 'volume-title': 'Hypervalent Iodine in Organic Synthesis', 'author': 'Varvoglis A.', 'year': '1997'} / Hypervalent Iodine in Organic Synthesis by Varvoglis A. (1997)
10.1021/cr940424+ / Chem. Rev. by Stang P. J. (1996)
{'key': 'ja991094jb00004/ja991094jb00004_3', 'volume-title': 'The Organic Chemistry of Polycoordinated Iodine', 'author': 'Varvoglis A.', 'year': '1992'} / The Organic Chemistry of Polycoordinated Iodine by Varvoglis A. (1992)
{'key': 'ja991094jb00004/ja991094jb00004_4', 'first-page': '811', 'volume-title': 'Supplement D', 'author': 'Koser G. F.', 'year': '1983'} / Supplement D by Koser G. F. (1983)
{'key': 'ja991094jb00005/ja991094jb00005_1', 'first-page': '1565', 'volume': '22', 'author': 'Ph IO', 'year': '1983', 'journal-title': 'Inorg. Chem.'} / Inorg. Chem. by Ph IO (1983)
{'key': 'ja991094jb00006/ja991094jb00006_1', 'first-page': '2368', 'volume': '2367', 'author': 'Carmalt C. J.', 'year': '1994', 'journal-title': 'J. Chem. Soc., Chem. Commun.'} / J. Chem. Soc., Chem. Commun. by Carmalt C. J. (1994)
10.1021/ja971048o / J. Am. Chem. Soc. by Boucher M. (1997)
10.1016/S0040-4039(97)10522-6 / Tetrahedron Lett. by Macikenas D. (1998)
10.1021/ja01278a056 / J. Am. Chem. Soc. by Compound (1938)
{'key': 'ja991094jb00011/ja991094jb00011_1', 'first-page': '1017', 'volume': '17', 'year': '1998', 'journal-title': 'Organometallics'} / Organometallics (1998)
{'key': 'ja991094jb00012/ja991094jb00012_1', 'first-page': '822', 'volume': '27', 'author': 'Katritzky A. R.', 'year': '1989', 'journal-title': 'Magn. Reson. Chem.'} / Magn. Reson. Chem. by Katritzky A. R. (1989)
10.1021/ic00116a012 / Inorg. Chem. by Mishra A. K. (1995)
{'key': 'ja991094jb00015/ja991094jb00015_2', 'first-page': '2753', 'volume': '116', 'author': 'Evans D. A.', 'year': '1994', 'journal-title': 'J. Am. Chem. Soc.'} / J. Am. Chem. Soc. by Evans D. A. (1994)
10.1021/ja00163a053 / J. Am. Chem. Soc. by Zhang W. (1990)
10.1021/ic00220a056 / Inorg. Chem. by Nappa M. J. (1985)
10.1021/ic00304a028 / Inorg. Chem. by Bressan M. (1989)
10.1002/(SICI)1521-3773(19990401)38:7<937::AID-ANIE937>3.0.CO;2-O / Angew. Chem., Int. Ed. Engl. by Francis M. B. (1999)
Recent exciting work has established that introduction of chiral dialkyl ether groups (for secondary bonding to I(III) center) into analogues of Koser's reagent ([PhI(OH)(OTs)]) can promote asymmetric oxytosylation reactions. See: (a) Hirt, U. H.; Spingler, B.; Wirth, T.J. Org. Chem.1998,63, 7674−7679. (b) Wirth, T.; Hirt, U. H.Tetrahedron Asym.1997,8, 23−26. (10.1021/jo980475x)

Dates

Type	When
Created	23 years, 1 month ago (July 26, 2002, 1:36 a.m.)
Deposited	3 years, 11 months ago (Sept. 23, 2021, 11:21 p.m.)
Indexed	1 week, 1 day ago (Aug. 28, 2025, 8:28 a.m.)
Issued	26 years, 1 month ago (July 16, 1999)
Published	26 years, 1 month ago (July 16, 1999)
Published Online	26 years, 1 month ago (July 16, 1999)
Published Print	26 years, 1 month ago (Aug. 1, 1999)

Funders 0

None

BibTeX

@article{Macikenas_1999, title={A New Class of Iodonium Ylides Engineered as Soluble Primary Oxo and Nitrene Sources}, volume={121}, ISSN={1520-5126}, url={http://dx.doi.org/10.1021/ja991094j}, DOI={10.1021/ja991094j}, number={30}, journal={Journal of the American Chemical Society}, publisher={American Chemical Society (ACS)}, author={Macikenas, Dainius and Skrzypczak-Jankun, Ewa and Protasiewicz, John D.}, year={1999}, month=jul, pages={7164–7165} }

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