Rotaxane-Stabilized Thiophosphonium Salt from Disulfide and Phosphine

Organic Letters

Volumn 5, Issue 26, 2003, Pages 4923-4925

  Oku, Tomoya ^a,b   Furusho, Yoshio ^a,b   Takata, Toshikazu ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; DISULFIDE; HEXAMETHYLPHOSPHORUSTRIAMIDE; PHOSPHINE; PHOSPHONIUM DERIVATIVE; ROTAXANE; THIOPHOSPHONIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; REACTION ANALYSIS; SPECTROSCOPY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0346025414     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035831z     Document Type: Article

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26. w = 0.110, GOF = 0.91, reflection/ parameter ratio = 24.87, max shift/error in final cycle = 0.002.
27. 1H NMR spectra. This seems to suggest that the nucleophiles preferentially attacked the P atom. If the nucleophiles attack the sulfur or the neighboring carbon atom, a new rotaxane is expected to be formed. This result shows that crown ether acts as an effective protecting group for both the sulfur and the contiguous carbon atoms that have strong electrophilicity to prevent the desulfurization reaction and to stabilize the thiophosphonium salt.