Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2002(10): 1344-1346
DOI: 10.1055/s-2002-33122
DOI: 10.1055/s-2002-33122
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Highly Efficient Synthesis of Methylenecyclopropane
Further Information
Received
19 February 2002
Publication Date:
01 August 2002 (online)
Publication History
Publication Date:
01 August 2002 (online)
Abstract
An efficient procedure for the preparation of methylenecyclopropane (3), a valuable starting material in organic synthesis, has been developed from methallyl chloride (1) and alkali metal [bis(trimethylsilyl)]amide [M(BTMSA) (M = Na, K), 2b,c]. The advantages of this new method are the higher yield of methylenecyclopropane up to 79% and a homogenous reaction mixture, i.e. both substrates are soluble in organic solvents such as toluene and dibutyl ether.
Key words
methylenecyclopropane - methallyl chloride - elimination
- 2
Fisher F.Applequist DE. J. Org. Chem. 1965, 30: 2089 - 3
Köster R.Arora S.Binger P. Liebigs. Ann. Chem. 1973, 1219 - 4
Krull IJ.Arnold DR. Org. Prep. Proced. Intl. 1969, 1: 283 - 5
Canbere P.Coudert G. Bull. Soc. Chim. Fr. 1971, 2234 - 6
Salaün JR.Champion J.Conia JM. Org. Synth. 1977, 57: 36 - Reviews:
-
7a
Brandi A.Goti A. Chem. Rev. 1998, 98: 589 -
7b
Binger P.Büch HM. Top. Curr. Chem. 1987, 135: 77 -
7c
Ohta T.Takaya H. Compreh. Org. Chem. 1991, 5: 1185 -
7d
Binger P.Schmidt Th. Houben-Weyl Vol. E17c:de Meijere A. Thieme Verlag; Stuttgart: 1997. p.2217 -
8a
Wannagat U.Niederprüm H. Chem. Ber. 1961, 94: 1540 -
8b
Krüger C.Rochow EG.Wannagat U. Chem. Ber. 1963, 96: 2132 -
10a
Köbrich G. Angew. Chem., Int. Ed. Engl. 1972, 11: 473 ; Angew. Chem. 1972, 84, 557 -
10b
Brinker UH.Misslitz U. Houben-Weyl Vol. E19b, Teil 1: Thieme Verlag; Stuttgart: 1989. p.337 -
11a
Julia M.Verpeaux J.-N.Zahneisen Th. Bull. Soc. Chim. Fr. 1994, 131: 539 -
11b
Wenkert E.Bakuzis P.Dynak JN.Swindell LS. Synth. Commun. 1979, 9: 11 -
11c
McDonald TL.Amirthaligam NB.O’Dell DE. J. Org. Chem. 1981, 46: 1504 - 12
Magid RM.Clarke TC.Duncan CD. J. Org. Chem. 1971, 36: 1320
References
Present address: Fachbereich Chemie der Universität Kaiserslautern, Postfach 3049, 67653 Kaiserslautern, Germany.
9Binger P.; Studiengesellschaft Kohle MbH, Ger. Offen. DE 4333491, 1995; Chem. Abstr. 1996, 122, 264949