I recently discovered a good textbook for those interested in organic chemistry: http://www.wiley.com/WileyCDA/WileyTitle/productCd-0470450339.html
This is geared towards intermediate undergraduate chemistry majors (preferably after they have finished a year-long course in Organic Chemistry), or can be used by the instructor to supplement the regular sophomore Organic course. The book gives a very broad-based coverage of the organic chemistry of the elements; thus the topic of this book can more correctly be described as “elemento-organic chemistry”. Since the emphasis is on the main-group elements, transition-metal organometallic chemistry is glossed over. Very detailed attention is given to the chemistry of the hypervalent main group elements (such as boron, carbon, silicon, sulfur, phosphorous, germanium, bismuth, iodine, and bromine), since that is the author’s area of expertise. Carbene chemistry (especially that of the stable, NHC (Arduengo) carbenes) has a chapter of its own. Brief mention of stereoelectronic effects as applied to conformation and reactivity of organic substrates is done in the overall context of bonding.
Unfortunately, there is little mention of carbocation chemistry (which is one of my areas of interest). I also feel the author could have been a little bit more attentive in citing the literature appropriately. While I do not doubt his knowledge of the chemistry presented, one of the major uses of a textbook is a primary tool for finding literature citations. To take a random example: If I wanted to find papers on the chemistry of low-valent iron, the first thing I would do would be to find a book or textbook on iron chemistry, flip to the chapter on low-valent iron, and look up the references for that chapter. Also, since this book was translated from Japanese, minor errors in translation and various other typos are scattered throughout. However, they do not impede understanding.
I would recommend this book to interested undergraduate and graduate students in organic chemistry. For instructors, this book can be used as a supplement for sophomore undergraduate chemistry and would make a perfect textbook for undergraduate advanced organic chemistry. At the graduate level, this can serve as an introduction to advanced topics, such as hypervalency, which are not usually taught at the undergraduate level.
It’s not that expensive on amazon: http://www.amazon.com/Organo-Group-Chemistry-Kin-ya-Akiba/dp/0470450339, only $73. This is cheap compared to the astronomical prices I have paid for books in years past.