Mechanistic aspects of the titanocene dichlonde-isopropyl grignard reduction of alkyl bromides

Rltatt J.A. and Kltchirg W. (1982) Mechanistic aspects of the titanocene dichlonde-isopropyl grignard reduction of alkyl bromides. Organometallics, 1 8: 1089-1093.

Author Rltatt J.A.
Kltchirg W.
Title Mechanistic aspects of the titanocene dichlonde-isopropyl grignard reduction of alkyl bromides
Journal name Organometallics   Check publisher's open access policy
ISSN 0276-7333
Publication date 1982-01-01
Sub-type Article (original research)
Volume 1
Issue 8
Start page 1089
End page 1093
Total pages 5
Subject 1604 Human Geography
1605 Policy and Administration
Abstract The stereodiemiatiy of the reductions of cis- and trans-4-methylcyclohyl-1-d bromide with the ayitem isopropybruigiiesiui bromidp-5% dicyclopendidyltitauium dichloride (argon) and of the unhbeled bromides with liaopropylmasnemunbronude icyc by 2H NMR analysis the resulting cis- and trans 4-melhyIcyclhsxane-I-d. Complet steraoequilibration occurs in some step and predominantly equatorial hydropcn (or deuterium) bslraclion by tbe pmumed 4-methylcyclubeiyl radical iindicated Radical Involvftmait . confirmed by the identification of substantial amounts of cydid hydrocarbnnn in the rduction the 6-bromo-hex-1-eneimd 6-bromo-hept-1-ene, whereas complet cydizaflun and bydrugen abslmclion ro provide 3-methyltethydrofuran charncterLwo tht reduction of 2-(allylcoxy)ethyl broinidfr Preiminary cipcrimentc that titanocene dichloride only feebly coulyxes the reduction of secondary bromides by todiura borohydride under aerobic conditions in N,N-di-methylformunide, iuch reductiooi Dpven hele procptdin with predominant inversion of confdialiun. Cyclized hydrocirbons from suitable bromo precursors (above) were not observed, indicating minor role for free radical in this system. A report that dicydoptntatlienyltilinium diohlorid exprience a dimethyl sulfoxide induced → σ rearrangement of both cyclopentidimtyl gmupi ii shown to be incorrect.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import - Archived
 
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Created: Tue, 23 Aug 2016, 14:35:16 EST by System User