ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Cob(I) alamin (1(I))-catalyzed reduction of the aldehyde 2 led to the two crystalline cyclopropanols 3 and 4 (see Scheme 2). The protolytic ring-opening starting from 3 produced the saturated aldehydes 6 and 7;8 was formed in traces only (see Scheme 3). The protolysis starting from 3 led, therefore, mainly to retention of configuration at the spiro C-atom (7); ring-opening with inversion was observed in traces only (8). Starting from 4, the protolysis produced 9 and 7; the absence of 8 showed this protolysis to proceed 9 and 7; the absence of 8 showed this protolysis to proceed exclusively with inversion of configuration at the spiro center. Of the p-bromobenzoate 5 (cf. Scheme 2) the structure has been determined by X-ray analysis.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19840670307
