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Tetrahedron Letters

Volumn 30, Issue 41, 1989, Pages 5579-5582

An efficient new method for the desulfonylation of β-keto phenylsulfones

(3) Smith III, Amos B a Hale, Karl J a McCauley Jr , John P a

a MONELL CHEMICAL SENSES CENTER (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001563784 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)93804-3 Document Type: Article

Times cited : (63)

References (14)

1
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- Smith¹ Hale²

2
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- For the isolation of FK506, see:
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 5031
- Tanaka¹ Kuroda² Marusawa³ Hatanaka⁴ Kino⁵ Goto⁶ Hashimoto⁷ Taga⁸

3
- 0000433217
- (1965) J. Am. Chem. Soc. , vol.87 , pp. 1345
- Corey¹ Chaykovsky²

4
- 49549126692
- (1976) Tetrahedron Lett. , vol.18 , pp. 3477
- Trost¹ Arndt² Strege³ Verhoeven⁴

5
- 33847804432
- (1974) J. Org. Chem. , vol.39 , pp. 2135
- Grieco¹ Masaki²

6
- 0000752703
- (1966) J. Am. Chem. Soc. , vol.88 , pp. 5498
- Russell¹ Mikol²

7
- 0343652274
- Preparation of substituted acetophenones from carboxylic acid esters
- (1974) Collection of Czechoslovak Chemical Communications , vol.39 , pp. 1216
- Pavlickova¹ Koutek² Velek³ Soucek⁴

8
- 33845374613
- (1986) J. Org. Chem. , vol.51 , pp. 1135
- Molander¹ Hahn²

9
- 84919137737
- 13C (100 or 62.9 MHz) NMR spectra. Elemental composition was determined by HRMS (parent ion identification) and/or by combustion analysis within 0.4 %.

10
- 3643120172
- Intramolecular attack by a benzylic radical on a sulfone oxygen atom followed by CS bond cleavage has been documented previously:
- (1975) Tetrahedron Lett. , vol.16 , pp. 3605
- Kelley¹ Carmack²

11
- 37049090508
- On Baldwin's kinetic barrier against 5-(enol-endo)-exo-trigonal closures: a comparison of ionic and analogous radical reactions, and a new synthesis of cyclopentanones
- α-Keto radicals have been proposed as intermediates in the triphenylstannane reduction of α-(phenylseleno) ketones:
- (1987) Journal of the Chemical Society, Chemical Communications , pp. 1520
- Clive¹ Cheshire²

12
- 84919137736
- An α-keto radical intermediate would not be expected to attack the terminus of the trisubstituted olefin in compound 1; this 5-endo-trig process would be disfavored according to Baldwin's rules; see: Baldwin, J.E. J. Chem. Soc., Chem. Comm.

13
- 37049091461
- Some guidelines for radical reactions
- Cyclobutane formation is also disfavored because it involves attack at the more substituted position of a trisubstituted olefin. For a detailed discussion of the rules for radical ring closure see:
- (1980) Journal of the Chemical Society, Chemical Communications , pp. 482
- Beckwith¹ Easton² Serelis³

14
- 0001646950
- 3SnCl, see:
- (1985) J. Org. Chem. , vol.50 , pp. 3846
- Kurth¹ O'Brien²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.