Abstract
AbstractTreatment of carbonyl compounds with SmI2 and methyl chloroformate in the presence of molecular sieves provides the cyclic carbonates or biscarbonates of pinacols. This one‐pot reaction proceeds rapidly even with aliphatic ketones. The stereochemistry obtained by this procedure is different from that of conventional pinacolic couplings.
References
60
Referenced
7
10.1021/cr00087a002
10.1016/B978-0-08-052349-1.00073-1
/ Comprehensive Organic Synthesis by Robertson G. M. (1991)10.1016/S0040-4020(01)86132-9
10.1002/anie.199600611
10.1021/cr950019y
- Fürstner A.;Csuk R.;Rohrer C.;Weidmann H.J. Chem. Soc. Perkin Trans 11988 1729and the references cited therein.
10.1016/S0040-4039(00)87103-8
10.1016/S0040-4039(00)81521-X
10.1016/0022-328X(83)85053-0
10.1016/S0022-328X(00)99769-9
10.1021/ja00203a027
10.1016/S0040-4039(00)92024-0
10.1016/S0040-4039(00)93437-3
10.1016/S0040-4020(01)96909-1
10.1021/ja00120a034
10.1021/ja962331a
10.1021/ja00529a028
10.1021/ja00083a017
-
Mukaiyama T. Sato T. Hanna J.Chem. Lett.1973 1041.
(
10.1246/cl.1973.1041
) 10.1021/jo00864a016
10.1016/0022-328X(84)85103-7
10.1021/jo00158a021
10.1016/S0040-4039(00)87657-1
10.1016/S0040-4039(00)80307-X
10.1016/S0040-4039(00)96822-9
10.1016/0040-4039(96)00462-5
10.1002/anie.198109111
-
Léonard E.;Doñach E.;Périchon J.J. Chem. Soc. Chem. Commun.1989 276.
(
10.1039/C39890000276
) 10.1021/ja00132a044
10.1021/jo00154a043
10.1021/jo00260a015
10.1016/S0040-4020(01)82098-6
10.5059/yukigoseikyokaishi.47.200
{'key': 'e_1_2_1_35_2', 'first-page': '15', 'volume': '24', 'author': 'Soderquist J. A.', 'year': '1991', 'journal-title': 'Aldrich. Acta'}
/ Aldrich. Acta by Soderquist J. A. (1991)10.1021/cr00009a002
10.1070/RC1994v063n04ABEH000088
10.1021/cr950019y
10.1016/S0040-4039(00)77601-5
10.1021/jo00360a058
-
Narasaka K. Inoue M. Yamada T.Chem. Lett.1986 1967.
(
10.1246/cl.1986.1967
) 10.1021/ja00187a093
10.1016/0925-8388(93)90229-G
10.1016/S0040-4039(00)93497-X
10.1021/jo961121d
10.1021/jo01267a085
10.1021/jo00911a028
10.1021/ja00537a059
-
Whitesell J. K.;Battacharaya A.;Aguilar D. A. Henke K.J. Chem. Soc. Chem. Commun.1982 988.
(
10.1039/c39820000988
) 10.1021/ja00212a037
10.1016/S0040-4020(01)80921-2
{'key': 'e_1_2_1_52_2', 'first-page': '104', 'volume-title': 'Protective Groups in Organic Synthesis', 'author': 'Greene T. W.'}
/ Protective Groups in Organic Synthesis by Greene T. W.10.1016/0040-4039(93)85085-B
10.1080/00397919408011189
10.1016/S0040-4039(00)82353-9
-
Teranishi K. Nakao H. Komoda A. Hisamatsu M. Yamada T.Synthesis1995 176.
(
10.1055/s-1995-3874
) 10.1021/jo00124a052
- Kundu B. Shukla M. Shukla S.J. Chem. Res. (S)1994 427.
10.1016/S0040-4039(00)92141-5
10.1021/jo00124a044
{'key': 'e_1_2_1_61_2', 'first-page': '494', 'volume-title': 'Mass Spectrometry of Organic Compounds', 'author': 'Budzikiewicz H.', 'year': '1967'}
/ Mass Spectrometry of Organic Compounds by Budzikiewicz H. (1967)
Dates
Type | When |
---|---|
Created | 10 years, 3 months ago (May 1, 2015, 3:18 p.m.) |
Deposited | 1 year, 9 months ago (Oct. 27, 2023, 11:11 p.m.) |
Indexed | 1 year, 9 months ago (Oct. 29, 2023, 12:35 a.m.) |
Issued | 28 years, 2 months ago (June 1, 1997) |
Published | 28 years, 2 months ago (June 1, 1997) |
Published Online | 11 years, 11 months ago (Sept. 24, 2013) |
Published Print | 28 years, 2 months ago (June 1, 1997) |
@article{Lu_1997, title={One‐Pot Formation of Carbonates from the Reactions of Carbonyl Compounds with Samarium Diiodide and Methyl Chloroformate}, volume={44}, ISSN={2192-6549}, url={http://dx.doi.org/10.1002/jccs.199700043}, DOI={10.1002/jccs.199700043}, number={3}, journal={Journal of the Chinese Chemical Society}, publisher={Wiley}, author={Lu, Ling and Fang, Jim‐Min and Lee, Gene‐Hsiang and Wang, Yu}, year={1997}, month=jun, pages={279–289} }