SCOPUS 정보 검색 플랫폼

Volumn 35, Issue 13, 1994, Pages 2017-2020

Acidic isomerization of vicinally substituted (cis)-acceptor-donor cyclopropanes via an open ring mechanism

b CNRS (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0028220912 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)73037-1 Document Type: Article

Times cited : (18)

References (18)

1
- 0000662936
- Bonding Properties of Cyclopropane and Their Chemical Consequences
- Int.Ed.
- (1979) Angewandte Chemie International Edition in English , vol.18 , pp. 809-826
- De¹

4
- 0012144739
- (1983) Tetrahedron Lett. , vol.24 , pp. 5521-5524
- Mioskowski¹ Manna² Falck³

6
- 0002631111
- For a review in the alkoxy donor group serie see
- (1980) Acc.Chem.Res. , vol.13 , pp. 27-31
- Wenkert¹

7
- 0027376442
- (1993) Tetrahedron Lett. , vol.34 , pp. 7405-7408
- Dechoux¹ Ebel² Jung³ Stambach⁴

8
- 0000569123
- One of the earliest report of configurationally stable cyclopropylanions bearing a carbonyl substituent came from Walborsky
- (1952) J.Am.Chem.Soc. , vol.74 , pp. 4962-4963
- Walborsky¹

9
- 0345249620
- (1962) J.Am.Chem.Soc. , vol.84 , pp. 2465-2466
- Walborsky¹ Youssef² Motes³

10
- 0001505175
- (1970) J.Am.Chem.Soc. , vol.92 , pp. 2445-2450
- Walborsky¹ Motes²

11
- 33947296297
- (1970) J.Am.Chem.Soc. , vol.92 , pp. 3697-3699
- Motes¹ Walborsky²

12
- 0011850110
- (1977) J.Am.Chem.Soc. , vol.99 , pp. 2631-2638
- Periasamy¹ Walborsky²

15
- 84912971421
- 3 using 0.1 mmole of the cyclopropane and 5 molar equivalents of trifluoroacetic acid at room temperature.

16
- 84912981269
- 1H NMR spectrum of the crude mixture. The methylene protons are part of an AMX system. The δppm values of the two methylene quartet protons are upshielded in the (trans)-cyclopropane, relative to the cis isomer. The stereochemistry of the trans isomer was confirmed by a strong nuclear Overhauser effect (nOe) between the α-carbonyl hydrogen and the two hydrogens of the hydroxymethylene function indicating a spatial proximity.

17
- 84913002537
- 3, 50 MHz) δ: 15.3 (HCHCHCH), 22.7 (OCCH), 27.3, CHCH [[Truncated]]

18
- 84912964011
- If a catalytic amount of TFA is used, the reaction proceeds, but much more slowly.

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