Abstract

ORGANIC PREPARATIONS AND PROCEDURES INT. 7(6), 283-290 (1975) PREPARATION OF 3-t-BUTYL-1,5-PENTANEDIOIC ACID AND OF 3-t-BUTYL-1,5-PENTANEDIOL DITOSYLATE + * W. R. Purdum and K. D. Berlin Department ofChemistr:y, Oklahoma State University, Stillwater, Oklahoma 74074 Six-membered heterocyclic systems possessing strategically located t- butyl substituents are of current interest with respect to conformational analysis. 1-6 Although a major portion of these investigations have dealt with heterocycles containing two heteroatoms, such as 1,3,2-dioxaphosphor- 4a,b inanes and trimethylene ~ulfites,~ the use of the 4-t-butyl substi- tuent to impart conformational stability to six-membered heterocycles with The paucity of only one heteroatom has received scant attention. 5y6 information in the latter case could be a result of a lack of synthetic procedures to obtain the desired t-butyl-substituted heterocycles. Although numerous methods exist for the introduction of a heteroatom, one major approach has involved an intramolecular cyclization of a 1,5-di- Two substituted pentane derivative with a selected heteroatom moiety. examples of this method have been reported in the preparations ofdiphenyl- phosphorinanium tosylate (I) 7 and the thiane 1-oxide (11). 8 CH 16 5 TosO- I 11 @ 1975 by Organic Preparations and Procedures, Inc. W. R. PURDUM AND K. D. BERLIN The introduction of a t-butyl substituent