Electrophilic cleavages in (CH3)3SnCH2M(CH3)3 (M = Sn, Ge, Si, C). 1. Product distribution

Hawker D.W. and Wells P.R. (1985) Electrophilic cleavages in (CH3)3SnCH2M(CH3)3 (M = Sn, Ge, Si, C). 1. Product distribution. Organometallics, 4 5: 821-825.

Author Hawker D.W.
Wells P.R.
Title Electrophilic cleavages in (CH3)3SnCH2M(CH3)3 (M = Sn, Ge, Si, C). 1. Product distribution
Journal name Organometallics   Check publisher's open access policy
ISSN 0276-7333
Publication date 1985-01-01
Sub-type Article (original research)
Volume 4
Issue 5
Start page 821
End page 825
Total pages 5
Subject 1604 Human Geography
1605 Policy and Administration
Abstract The extent to which Sn-CH2 and/or Sn-CH3 cleavage occurs in (CH3)3SnCH2M(CH3)3 (M = Sn, Ge, Si) in reactions with several electrophiles has been determined. With iodine and with bromine in various solvents both sites are attacked with Sn-CH2 cleavage favored for nonpolar solvents and for M = Sn. Protolysis leads to Sn-CH2 cleavage only, and this site appears to be activated by the (CH3)3M groups. On the other hand organometallic electrophiles exclusively attack the Sn-CH3 groups and the (CH3)3MCH2 groups are deactivating. With all reagents only the Sn-CH3 groups are reactive in (CH3)3SnCH2C(CH3)3. The complex mechanistic situation for halogenolysis can lead to variations in the relative reactivities of various sites during reaction and introduce serious errors into internal selectivity measurements.
Q-Index Code C1
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import - Archived
 
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Created: Tue, 06 Sep 2016, 11:17:13 EST by System User