In:
Israel Journal of Chemistry, Wiley, Vol. 29, No. 2-3 ( 1989-01), p. 131-135
Abstract:
A stereospecific 18 O‐labelling study shows that the syn ‐hydroxy group is preferentially lost from the syn, anti ‐title diol upon i ‐C 4 H 10 chemical ionization, indicating occurrence of a stereoelectronic effect in this process. A collision‐induced dissociation study of deuterium‐ and 18 O‐labelled analogs shows that a symmetrical ether structure is not formed in the above process by an S N i mechanism. This result leads to the conclusion that the stereoelectronic assistance of the anti ‐OH group in the loss of the syn ‐hydroxyl is expressed either in a weak transition state interaction or by other processes such as β‐elimination via hydrogen transfer with concomitant double bond formation.
Type of Medium:
Online Resource
ISSN:
0021-2148
,
1869-5868
DOI:
10.1002/ijch.v29:2-3
DOI:
10.1002/ijch.198900019
Language:
English
Publisher:
Wiley
Publication Date:
1989
detail.hit.zdb_id:
2066481-3
Permalink